Benzyl mercaptan → HCID 86588936, compound

HRID 1369027Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[CH2:10]([SH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[CH:10]([S:17][CH:8](/[CH:9]=[CH:8]\[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7509Benzyl mercaptan

HCID 70118Benzene, 1-chloro-4-ethynyl-

HCID 5360545Sodium

Product 1

HCID 86588936HCID 86588936, compound

Procedure

A solution of 4-chlorophenylacetylene (0.02 mol) and benzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) was subjected to the General Procedure to form Z-4-chlorostyryl benzylsulfide. The title compound was obtained in 74% yield following oxidation. 1HNMR (CDC13) δ4.55 (2H, s), 6.66 (1H, d, JH,H=12.12), 7.16-7.65 (9H aromatic+1H ethylenic).

Sources & evidence

ORD record: ord-e3ef16e43fbe49738dc7d5609ee813a2
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06576675B1

Reaction notes

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