p-Chlorothiophenol → HCID 70380103, compound

HRID 1194995Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH3:9][CH:10]([OH:13])[C:11]#[CH:12].[OH-].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]/[CH:12]=[CH:11]\[CH:10]([OH:13])[CH3:9])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7815p-Chlorothiophenol

HCID 14797Potassium Hydroxide

HCID 162393-Butyn-2-ol

Product 1

HCID 70380103HCID 70380103, compound

Conditions

Temperature: 100 °C

Procedure

A mixture of 4.5 g (31.1 mmol) of p-chlorothiophenol, 3.7 g (4.2 ml; 37.3 mmol) of 3-butyn-2-ol and 150 mg of powdered potassium hydroxide is heated to 100° C for 20 minutes. The brown crude product is then chromatographed on silica gel (ethyl acetate/hexane). There is obtained pure rac-(Z)-4-[(p-chlorophenyl)thio]-3-buten-2-ol.

Workup

customThe brown crude product is then chromatographed on silica gel (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-27bb3e7f7ce84da18c098f3b9821825b
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816581

Reaction notes

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