p-Ethynyltoluene → Z-4-methylstyryl 2-chlorobenzylsulfide

HRID 431160

Reaktionsgleichung

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

Komponenten

Edukt 3

HCID 13018p-Ethynyltoluene

HCID 5807592-Chlorobenzyl mercaptan

HCID 5360545Sodium

Produkt 1

HCID 86588949Z-4-methylstyryl 2-chlorobenzylsulfide

Versuchsvorschrift

A solution of 4-methylphenylacetylene (0.02 mol) and 2-chlorobenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) was subjected to Procedure 2 to form (Z)-4-methylstyryl 2-chlorobenzylsulfide. The title compound was obtained in 76% yield following oxidation. 1HNMR (CDC13) δ2.50 (3H, s), 4.58 (2H, s), 6.80 (1H, d, JH,H=11.88), 7.20-7.63 (9H aromatic+1H ethylenic).

Quellen und Nachweise

ORD-Eintrag: ord-1c4f06218d0a44e8b12c233a2ad684bc
Quelldatensatz: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06656973B2

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