3-(2-Chlorophenyl)acrylic acid → 3-(2-Chlorophenyl)propanoic acid
Reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7]>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Chlorocinnamic acid (26 g) (ex Aldrich) in glacial acetic acid (250 ml) was subjected to hydrogenation at 45 psi in the presence of 10% palladium/charcoal. Conventional work-up gave 3-(2-chlorophenyl)propanoic acid (26.3 g) which was added to polyphosphoric acid (220 g) at 80° under nitrogen. After stirring for 2 hours at 80° the mixture was allowed to cool and added to water, ether extraction and conventional work up gave 4-chloroindan-1-one as a brown solid (10 g).
Sources & evidence
- ORD record
- ord-713cbf6466094e2c9efb39f32f3c03f6
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05180737
Reaction notes
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