Dimethyl Sulfide → 2-Methoxy-α-oxobenzeneacetic acid

HRID 1585232Notes

Reaction equation

HRID 1585232 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=C)[C:13]([OH:15])=[O:14].CSC>ClCCl>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:1])[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 10921070HCID 10921070, compound

Product 1

HCID 34311012-Methoxy-α-oxobenzeneacetic acidYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stream of ozone is sparged at -75° C. for 3 hours 30 minutes into a solution of 1 g (5.62 mmol) of 2-(2-methoxyphenyl)acrylic acid, obtained under the conditions described in Example 38, in dichloromethane. 1.66 cm3 (22.5 mmol) of dimethyl sulphide are added and stirring is continued, the temperature being allowed to rise to the region of 20° C. After concentrating the reaction mixture to dryness, 0.7 g (69%) of (2-methoxyphenyl)oxoacetic acid is obtained in the form of crystals, the characteristics of which are as follows: mass spectrum (E.I.) M/Z=180 (M+)

Workup

  1. customobtained under the conditions
  2. customto rise to the region of 20° C
  3. concentrationAfter concentrating the reaction mixture to dryness

Sources & evidence

ORD record
ord-8625c8d040d6467099fac1d0334d60a3
Source dataset
uspto-grants-1999_08
Patent number
US05936097

Reaction notes

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