3-Chlorobenzaldehyde → 2-[2-(3-Chlorophenyl)-vinyl]-4-methoxybenzoic acid

HRID 473453Notes

Reaction equation

HRID 473453 reaction equation
Br[CH2:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH:37]=O.C[O-].[Na+]>CO>[Cl:33][C:34]1[CH:35]=[C:36]([CH:37]=[CH:2][C:3]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])[CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 11776TriphenylphosphineHCID 10942334Sodium MethoxideHCID 225942062-Bromomethyl-4-methoxybenzoic acid

Product 1

HCID 674972072-[2-(3-Chlorophenyl)-vinyl]-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

For the synthesis of the title compound, 45.6 g (0.186 mol) of 2-bromomethyl-4-methoxybenzoic acid, 48.8 g (0.186 mol) of triphenylphosphine, 26.1 g (0.186 mol) of 3-chlorobenzaldehyde and 84.0 g (0.435 mol) of NaOMe (28%) in 150 ml of methanol are reacted by method I. Purification is carried out by recrystallization from methanol at 4° C.

Sources & evidence

ORD record
ord-57c08588096146c28ca1ab6f0fe97377
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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