GB1389802A - production of optically active alpha-phenylpropionaldehyde - Google Patents
production of optically active alpha-phenylpropionaldehydeInfo
- Publication number
- GB1389802A GB1389802A GB1363473A GB1363473A GB1389802A GB 1389802 A GB1389802 A GB 1389802A GB 1363473 A GB1363473 A GB 1363473A GB 1363473 A GB1363473 A GB 1363473A GB 1389802 A GB1389802 A GB 1389802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine
- optically active
- phenyl
- methyl
- phenylpropionaldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 title abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 4
- 239000010948 rhodium Substances 0.000 abstract 4
- 229910052703 rhodium Inorganic materials 0.000 abstract 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- LSDSTZMZQGGDOP-UHFFFAOYSA-N benzyl-methyl-phenylphosphane Chemical compound C=1C=CC=CC=1P(C)CC1=CC=CC=C1 LSDSTZMZQGGDOP-UHFFFAOYSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- -1 phenyl-p-toluyl- Chemical group 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1389802 α-Phenyl propionaldehyde AGENCY OF INDUSTRIAL SCIENCE & TECHNOLOGY 21 March 1973 [6 April 1972] 13634/73 Heading C2C Optically active α-phenylpropionaldehyde is prepared by the reaction of styrene with carbon monoxide and hydrogen by causing the reaction to proceed in the presence of a rhodium catalyst and an optically active phosphine. The phosphine is used in an amount in excess of that required to produce a complex of the formula Rh.H(CO)(PR 3 ) in which PR 3 denotes the optically active phosphine. The rhodium catalyst may be metallic rhodium or a salt of an inorganic or organic acid. Suitable optically active phosphines are, e.g. methyl, -ethyl-nbutyl phosphine, phenyl-p-toluyl-#-naphthyl phosphine, methyl - benzyl - phenyl - phosphine and anisyl-methyl-phenyl-phosphine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3390072A JPS5037181B2 (en) | 1972-04-06 | 1972-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1389802A true GB1389802A (en) | 1975-04-09 |
Family
ID=12399383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1363473A Expired GB1389802A (en) | 1972-04-06 | 1973-03-21 | production of optically active alpha-phenylpropionaldehyde |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5037181B2 (en) |
| GB (1) | GB1389802A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360938A (en) * | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| US5475146A (en) * | 1993-09-02 | 1995-12-12 | E. I. Du Pont De Nemours And Company | Enantioselective hydroformylation |
| US5481006A (en) * | 1994-01-11 | 1996-01-02 | E. I. Du Pont De Nemours And Company | Selective asymmetric hydrogenation of dehydroamino acid derivatives using rhodium and iridium diphosphinite carbohydrate catalyst compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5260491A (en) * | 1990-09-24 | 1993-11-09 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
-
1972
- 1972-04-06 JP JP3390072A patent/JPS5037181B2/ja not_active Expired
-
1973
- 1973-03-21 GB GB1363473A patent/GB1389802A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360938A (en) * | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| US5491266A (en) * | 1991-08-21 | 1996-02-13 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| US5475146A (en) * | 1993-09-02 | 1995-12-12 | E. I. Du Pont De Nemours And Company | Enantioselective hydroformylation |
| US5574171A (en) * | 1993-09-02 | 1996-11-12 | E. I. Du Pont De Nemours And Company | Enantioselective hydroformylation |
| US5481006A (en) * | 1994-01-11 | 1996-01-02 | E. I. Du Pont De Nemours And Company | Selective asymmetric hydrogenation of dehydroamino acid derivatives using rhodium and iridium diphosphinite carbohydrate catalyst compositions |
| US5510507A (en) * | 1994-01-11 | 1996-04-23 | E. I. Du Pont De Nemours And Company | Selective asymmetric hydrogenation of dehydroamino acid derivatives using rhodium and iridium diphosphinite carbohydrate catalyst compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4899131A (en) | 1973-12-15 |
| JPS5037181B2 (en) | 1975-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |