p-Ethynyltoluene → HCID 86588948, compound

HRID 736563Notes

Reaction equation

HRID 736563 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][SH:16])=[CH:13][CH:12]=1.[Na]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[CH:15]([S:16][CH:15](/[CH:9]=[CH:8]\[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)[C:14]2[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 13018p-EthynyltolueneHCID 804094-Chlorobenzyl mercaptanHCID 5360545Sodium

Product 1

HCID 86588948HCID 86588948, compound

Procedure

A solution of 4-methylphenylacetylene (0.02 mol) and 4-chlorobenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) was subjected to Procedure 2 to form (Z)-4-methylstyryl 4-chlorobenzylsulfide. The title compound was obtained in 74% yield following oxidation. 1HNMR (CDC13) δ2.46 (3H, s), 4.64 (2H, s), 6.75 (1H, d, JH,H=12.21), 7.18-7.57 (9H aromatic+1H ethylenic).

Sources & evidence

ORD record
ord-434a67f07c9940c99212f4a986b17083
Source dataset
uspto-grants-2009_09
Patent number
US07595347B2

Reaction notes

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