Phthalide → 2-[(Phenylsulfanyl)methyl]benzoic acid

HRID 1065421Notes

Reaction equation

HRID 1065421 reaction equation
[C:1]1([C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][O:3]1)=[O:2].[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[O-].[K+]>CO>[C:11]1([S:17][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:1]([OH:3])=[O:2])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6885PhthalideHCID 7969ThiophenolHCID 23664618Potassium methoxide

Product 1

HCID 743372-[(Phenylsulfanyl)methyl]benzoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 67.1 gm of phthalide, 51.3 ml of thiophenol, 35.1 gm of potassium methylate and 250 ml of methanol was refluxed. Subsequently, the obtained 2-(phenylmercapto-methyl) -benzoic acid (yield: 78% of theory, m.p. 108°-110° C.) was esterified with methanol/thionylchloride by standing at -40° C. After standing overnight at room temperature, methyl 2-(phenylmercapto-methyl)-benzoate (yield: 89% of theory, b.p. 145° C. at 0.07 mm Hg) was obtained, which was converted into 2-(phenylmercapto-methyl)-phenyl carbinol (yield: 97% of theory, m.p. 64°-65° C.) by reduction with lithium aluminum hydride in diethyl ether.

Workup

  1. temperaturewas refluxed

Sources & evidence

ORD record
ord-a102a498f436490eb747d5c54d7d2a6b
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

Loading…