4-Methoxystyrene → 1-(4-methoxyphenyl)ethyl Dithiobenzoate

HRID 1297479Notes

Reaction equation

HRID 1297479 reaction equation
[C:1]([SH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH2:11]>C(Cl)(Cl)(Cl)Cl>[C:1]([S:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH3:11])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 125074-MethoxystyreneHCID 67141Benzenecarbodithioic acid

Product 1

HCID 178661071-(4-methoxyphenyl)ethyl DithiobenzoateYield 53%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of dithiobenzoic acid (3.6 g), 4-vinylanisole (2.9 g) and carbon tetrachloride (20 mL) were heated at 70° C. overnight. The solvent was evaporated and the residue subjected to column chromatography (aluminium oxide (activity III) column, 2% diethyl ether in n-hexane eluent) which gave the title compound (53% yield). 1H-nmr (CDCl3) d (ppm): 1.80 (d, 3H, SCHCH3); 3.80 (s, 3H, OCH3); 5.22 (q, 1H, SCHCH3) and 6.88-7.97 (m, 9H, ArH).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b9924380691d4a6ba73e755688f00a7d
Source dataset
uspto-grants-2007_07
Patent number
US07250479B2

Reaction notes

Loading…