2,4-Di-tert-butylphenol → HCID 86733273, compound

HRID 1606317Notes

Reaction equation

HRID 1606317 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([C:20]#[C:21][C:22]([O:24][CH3:25])=[O:23])=[O:19]>[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[CH3:16][O:17][C:18](=[O:19])/[C:20](/[O:15][C:6]1[CH:7]=[CH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:21]/[C:22]([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 73112,4-Di-tert-butylphenolHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 86733273HCID 86733273, compound

Reagents, catalysts & solvents 1

HCID 66854Benzyltrimethylammonium hydroxideCatalyst

Procedure

A mixture of 5 parts of 2,4-di-t-butylphenol, 3.55 parts of acetylene dicarboxylic acid dimethyl ester and four drops of benzyl-trimethylammonium hyroxide were heated on a steam bath for 20 min. The 2,4-di-t-butylphenoxyfumaric acid dimethyl ester formed was hydrolysed by heating with 2.8 parts of sodium hydroxide in 15 parts by volume of water and 8 parts by volume of methanol. The hydrolysis was complete when one layer was obtained. The methanol was boiled off and the solution was cooled and acidified with concentrated hydrochloric acid. The crude 2,4-di-t-butylphenoxyfumaric acid was liberated as an oil, and was extracted into ether. This acid was purified by extraction with sodium bicarbonate solution which was washed well with ether. Acidification of the sodium bicarbonate solution gave the purified fumaric acid which was extracted again into ether. The dried ether extracts were evaporated to give the fumaric acid as an oil.

Workup

  1. temperaturewere heated on a steam bath for 20 min

Sources & evidence

ORD record
ord-cdebb3b664854d4a8fae4623a07a1f1c
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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