Carbon Dioxide → 3-[4-(methylsulfanyl)phenyl]acrylic acid

HRID 750981Notes

Reaction equation

HRID 750981 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].C(=O)=O.Cl>N1C=CC=CC=1>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 6065043-[4-(methylsulfanyl)phenyl]acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 50.70 g (0.33 mol) 4-methylsulfanyl-benzaldehyde, 39.65 g (0.38 mol) malonic acid 3.25 g (0.04 mmol) piperidine and 150 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (5 h). The reaction mixture was poured into a solution of 750 ml ice water and 190 ml 6N HCl. The precipitate was isolated, washed with water, then with n-heptane and dried at 50° C. Yield: 60.0 g (93%) 3-(4-methylsulfanyl-phenyl)-acrylic acid as a light brown solid melting at 163-165° C.

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-edae30c36a1249619e00bc9ff37a9ce8
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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