Carbon Dioxide → 3-{4-[(Trifluoromethyl)sulfanyl]phenyl}prop-2-enoic acid

HRID 750939Notes

Reaction equation

HRID 750939 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([F:4])[F:3].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[F:1][C:2]([S:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:15][C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1)([F:4])[F:3]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 27778464-[(Trifluoromethyl)sulfanyl]benzaldehyde

Product 1

HCID 533956353-{4-[(Trifluoromethyl)sulfanyl]phenyl}prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5.42 g (26.3 mmol) 4-trifluoromethylsulfanyl-benzaldehyde, 3.12 g (30.0 mmol) malonic acid, 0.26 g (3.0 mmol) piperidine and 12.0 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (5 h). The reaction mixture was poured into a solution of 50 ml ice water and 15 ml 6N HCl. The precipitate was isolated, washed with water, then with n-heptane and dried at 50° C. Yield: 5.9 g (85%) 3-(4-Trifluoromethylsulfanyl-phenyl)-acrylic acid.

Workup

  1. custom(5 h)
  2. customThe precipitate was isolated
  3. washwashed with water
  4. dry with materialwith n-heptane and dried at 50° C

Sources & evidence

ORD record
ord-f683912ab78648368bbc7d6546a62036
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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