Potassium Carbonate → 4-[2-Cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl ester

HRID 1816181Notes

Reaction equation

HRID 1816181 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:22]([C:23]#[N:24])[C:19]2[CH:20]=[CH:21][C:16]([O:15][C:14]([F:13])([F:25])[F:26])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 1426764-(Trifluoromethoxy)phenylacetonitrile

Product 1

HCID 674834364-[2-Cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl esterYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

4-Formylbenzoic acid methyl ester (8.60 g, 52.39 mmol) was dissolved in warm methanol (50 mL) and 4-trifluoromethoxyphenylacetonitrile (10.54 g, 52.39 mmol) was added. The mixture was stirred and potassium carbonate (7.75 g, 56.05 mmol) was added. The mixture was heated to 60° C. and more methanol (20 mL) was added and stirring was continued for 1 hour. The precipitate was filtered off and added in small portions to a stirred and cold 4 M hydrochloric acid solution. The precipitate was filtered off, washed with water and dried to afford 14.4 g (79%) of 4-[2-cyano-2-(4-trifluoromethoxyphenyl)vinyl]benzoic acid methyl ester.

Workup

  1. stirringstirring
  2. filtrationThe precipitate was filtered off
  3. additionadded in small portions to
  4. stirringa stirred
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-844525af54ca4e42a2fe599d6a9a42be
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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