Chloroacetone → 3-(2-Oxo-propylsulfanyl)-benzoic acid

HRID 1466820Notes

Reaction equation

HRID 1466820 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(N(CC)CC)C.Cl[CH2:19][C:20](=[O:22])[CH3:21]>C1COCC1>[O:22]=[C:20]([CH3:21])[CH2:19][S:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 667650833-(2-Oxo-propylsulfanyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Mercapto-benzoic acid (5.0 g, 32.3 mmol) and triethylamine (11.3 mL, 81.1 mmol) were dissolved in THF at 0° C. Chloroacetone (2.7 mL, 33.9 mmol) was then added and the reaction was allowed to slowly warm to room temperature as it stirred overnight. Standard aqueous workup afforded the title compound which was brought forward to the next step without further purification.

Sources & evidence

ORD record
ord-8a16356137fb44d1ac8a94f77cf7ccce
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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