Thioglycolic Acid → 2-Benzhydrylsulfanylacetic acid

HRID 1987699Notes

Reaction equation

HRID 1987699 reaction equation
[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([OH:19])(=[O:18])[CH2:16][SH:17]>>[CH:1]([S:17][CH2:16][C:15]([OH:19])=[O:18])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1133Thioglycolic AcidHCID 7037Benzhydrol

Product 1

HCID 20778862-Benzhydrylsulfanylacetic acidYield 99%

Procedure

This compound was prepared according to the procedure of Prisinzano. (Prisinzano, T.; Podobinski, J.; Tidgewell, K.; Luo, M.; Swenson, D. Tetrahedron: Asymmetry 2004, 15, 1053-1058). The synthesis employed benzhydrol (50.0 g, 271.4 mmol) and thioglycolic acid (25.0 g, 271.4 mmol) to give the title compound as a white solid: 69.2 g (99% yield); mp 126-129° C. Spectroscopic data was identical to lit. (Prisinzano, T.; Podobinski, J.; Tidgewell, K.; Luo, M.; Swenson, D. Tetrahedron: Asymmetry 2004, 15, 1053-1058).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-089478f3b948481082db894e38c9d5b4
Source dataset
uspto-grants-2009_06
Patent number
US07553646B2

Reaction notes

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