Ethylene carbonate → 2-(Phenylthio)ethanol

HRID 916893Notes

Reaction equation

[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH2:12][CH2:11]OC1=O>>[C:1]1([S:7][CH2:11][CH2:12][OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 7303Ethylene carbonate

HCID 7969Thiophenol

Product 1

HCID 696852-(Phenylthio)ethanol

Procedure

Benzenethiol is reacted with 1,3-dioxolan-2-one to form 2-(phenylthio)ethanol. The 2-(phenylthio)ethanol is isolated and then converted to 2-(phenylthio)ethanethiol using triphenylphosphine, diisopropyl azodicarboxylate (DIAD), and thiolacetic acid followed by hydrolysis of the resulting acetate with potassium hydoxide in methanol.

Sources & evidence

ORD record: ord-b9fa317545da43eba563c8ceea1dafa7
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271283B2

Reaction notes

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