Sodium → (Z)-3,4-dihydroxystyryl-2,4,6-trimethoxybenzylsulfide

HRID 1019235Notes

Reaction equation

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

Participants

Reactant 3

HCID 5360545Sodium

HCID 10608677(2,4,6-Trimethoxyphenyl)methanethiol

HCID 226037784-Ethynylbenzene-1,2-diol

Product 1

HCID 86585666(Z)-3,4-dihydroxystyryl-2,4,6-trimethoxybenzylsulfide

Procedure

A solution of 3,4-dihydroxyphenylacetylene (0.02 mol), 2,4,6-trimethoxybenzyl mercaptan (0.02 mol) and metallic sodium (0.02 g atom) is subjected to General Procedure 2 to form (Z)-3,4-dihydroxystyryl-2,4,6-trimethoxybenzylsulfide. The title compound is obtained following oxidation of the sulfide, according to General Procedure 2.

Sources & evidence

ORD record: ord-c762ce58401642f0a9a824cd9c83052e
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486210B2

Reaction notes

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