Alpha-Methylstyrene → Cumyl dithiobenzoate

HRID 1445966

Reaction equation

HRID 1445966 reaction equation
[C:1]([SH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH2:12]>C(Cl)(Cl)(Cl)Cl>[C:1]([S:9][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:10])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7407Alpha-MethylstyreneHCID 67141Benzenecarbodithioic acid

Product 1

HCID 11065602Cumyl dithiobenzoateYield 32.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of dithiobenzoic acid (10.59 g), a-methylstyrene (10 g) and carbon tetrachloride (40 mL) was heated at 70° C. for 4 hours. The resultant mixture was reduced to a crude oil which was purified by column chromatography (aluminium oxide (activity III), n-hexane eluent) to give 2-phenylprop-2-yl dithiobenzoate (5) (6.1 g, 32.6% yield) as a dark purple oil. 1H-nmr (CDCl3) d (ppm): 2.03 (s, 6H); 7.20-7.60 (m, 8H) and 7.86 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-0f4f4fb382c84fd69d88914adce93fb6
Source dataset
uspto-grants-2010_02
Patent number
US07666962B2

Linked notes

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