Vinyl Acetate → 1-Acetoxyethyl dithiobenzoate

HRID 1444812

Reaction equation

HRID 1444812 reaction equation
[C:1]([SH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:13][CH:14]=[CH2:15])(=[O:12])[CH3:11]>C(Cl)(Cl)(Cl)Cl>[C:1]([S:9][CH:14]([O:13][C:10](=[O:12])[CH3:11])[CH3:15])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 67141Benzenecarbodithioic acid

Product 1

HCID 99428351-Acetoxyethyl dithiobenzoateYield 51.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of dithiobenzoic acid (4 g), vinyl acetate (10 mL) and carbon tetrachloride (15 mL) was heated at 70° C. for 16 hours. The resultant mixture was reduced and the residue purified by column chromatography (aluminium oxide column (activity III), n-hexane eluent) to give 1-acetoxyethyl dithiobenzoate (6) (3.21 g, 51.5% yield) as a dark red oil. 1H-nmr (CDCl3) d (ppm): 1.80 (d, 3H); 2.09 (s, 3H); 6.75 (q, 1H); 7.34-7.60 (m, 3H) and 7.97 (m, 2H).

Workup

  1. customthe residue purified by column chromatography (aluminium oxide column (activity III), n-hexane eluent)

Sources & evidence

ORD record
ord-49e5eb8d18d34891b53c034ea1359fe2
Source dataset
uspto-grants-2010_02
Patent number
US07662986B2

Linked notes

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