2,4-Dichlorobenzenemethanethiol → (Z)-3-methoxy-4-acetoxystyryl-2,4-dichlorobenzylsulfide

HRID 2308057Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[CH:14])[CH:6]=[CH:7][C:8]=1[O:9][C:10](=[O:12])[CH3:11].[Cl:15][C:16]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:17]=1[CH2:18][SH:19].[Na]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][C:10](=[O:12])[CH3:11])/[CH:13]=[CH:14]\[CH:18]([S:19][CH:18](/[CH:14]=[CH:13]\[C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10](=[O:12])[CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:17]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:16]=1[Cl:15])[C:17]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:16]=1[Cl:15]

Participants

Reactant 3

HCID 957562,4-Dichlorobenzenemethanethiol

HCID 5360545Sodium

HCID 226038063-Methoxy-4-acetoxyphenylacetylene

Product 1

HCID 86593396(Z)-3-methoxy-4-acetoxystyryl-2,4-dichlorobenzylsulfide

Procedure

A solution of 3-methoxy-4-acetoxyphenylacetylene (0.02 mol), 2,4-dichlorobenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) is subjected to the General Procedure to form (Z)-3-methoxy-4-acetoxystyryl-2,4-dichlorobenzylsulfide. The title compound is obtained following oxidation of the sulfide, according to the General Procedure.

Sources & evidence

ORD record: ord-3233eb134c5341b992c6299401e27555
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833480B2

Reaction notes

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