Acetone → Benzyl 2-(benzylsulfanyl)benzoate

Reaction equation

[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].N12CCCN=[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:30]C(C)=O>>[CH2:22]([O:9][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH2:30][C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Reactant 4

HCID 180Acetone

HCID 54432-Mercaptobenzoic Acid

HCID 7498Benzyl Bromide

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 802018Benzyl 2-(benzylsulfanyl)benzoate

Procedure

A solution of thiosalicylic acid 1 (2.0 g, 13.0 mmol) in 13 mL of acetone was treated with 1,8-Diazabicyclo [5.4.0]undec-7-ene (7.8 mL, 52 mmol) and benzylbromide (6.2 mL, 52 mmol). The reaction was stirred at room temperature for 50 minutes. The mixture was concentrated under vacuum to remove the acetone. Water was added and the mixture was extracted with EtOAc (3X). The organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid without purification.