2,6-Di-tert-butyl-4-mercaptophenol → Dimethyl 2-(3,5-di-tert-butyl-4-hydroxyphenylthio)succinate

HRID 464441Notes

Reaction equation

HRID 464441 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:17]([O:25][CH3:26])(=[O:24])/[CH:18]=[CH:19]\[C:20]([O:22][CH3:23])=[O:21]>C(N(CC)CC)C>[C:1]([C:5]1[CH:10]=[C:9]([S:11][CH:19]([CH2:18][C:17]([O:25][CH3:26])=[O:24])[C:20]([O:22][CH3:23])=[O:21])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 5271565Dimethyl maleate

Product 1

HCID 20255224Dimethyl 2-(3,5-di-tert-butyl-4-hydroxyphenylthio)succinateYield 80%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

The procedure of Example 1 is repeated using 23.84 grams of 2,6-di-tert-butyl-4-mercaptophenol, 14.41 grams of dimethyl maleate, and 0.5 grams of triethylamine. The product is recrystallized from heptane to give 30.44 grams (80% yield) of white solid, m.p. 94°-96° C.

Workup

  1. customThe product is recrystallized from heptane

Sources & evidence

ORD record
ord-3e0e1dc1773f47ecb2ad2414b110066e
Source dataset
uspto-grants-1985_10
Patent number
US04547539

Reaction notes

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