2-(2-Methylbenzyl)acrylic acid → 2-Acetylthiomethyl-3-(2-methylphenyl)propionic acid

HRID 1651717Notes

Reaction equation

HRID 1651717 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7].[C:14]([OH:17])(=[S:16])[CH3:15]>>[C:14]([S:16][CH2:9][CH:5]([CH2:4][C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][C:2]=1[CH3:1])[C:6]([OH:8])=[O:7])(=[O:17])[CH3:15]

Participants

3

Reactant 2

HCID 104648332-(2-Methylbenzyl)acrylic acidHCID 178418634HCID 178418634, compound

Product 1

HCID 100607772-Acetylthiomethyl-3-(2-methylphenyl)propionic acid

Procedure

To the acid from Step 3 (11.4 g, 65 mmol) add thioacetic acid (9.8 g, 129 mmol). After 3 days, concentrate, treat with toluene, and concentrate again to obtain a solid. Recrystallize from CH2Cl2 :hexane to obtain the title compound, m.p. 63°-70°.

Workup

  1. concentrationconcentrate
  2. additiontreat with toluene
  3. concentrationconcentrate again
  4. customto obtain a solid
  5. customRecrystallize from CH2Cl2

Sources & evidence

ORD record
ord-f45c7dfaeacb4e59a3e7ec2084fd0a19
Source dataset
uspto-grants-1990_05
Patent number
US04929641

Reaction notes

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