Water → [3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid

HRID 1466754

Reaction equation

HRID 1466754 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:13][C:14](=[O:16])[CH3:15].C(N(CC)C(C)C)(C)C.O>C1COCC1>[O:16]=[C:14]([CH3:15])[CH2:13][S:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 81531DiisopropylethylamineHCID 35431562-(3-Mercaptophenyl)acetic acid

Product 1

HCID 66765032[3-(2-Oxo-propylsulfanyl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Mercaptophenylacetic acid (3.0 g, 17.9 mmol) and chloroacetone (1.5 mL, 18.8 mmol) were combined in THF (100 mL) then a solution of N,N-diisopropylethylamine (10.9 mL, 62.7 mmol) in THF (100 mL) was added by addition funnel over the course of 20 minutes at room temperature. After 2 hours H2O (100 mL) was added and the reaction mixture was worked up to give the title compound as a solid.

Sources & evidence

ORD record
ord-43f2b3ce0f734867bc89fec3f9b9d4f8
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Linked notes

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