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

HRID 973262Notes

Reaction equation

HRID 973262 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 hydroxide 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-9ed262fbcd2749ad901670b6e6173f70
Source dataset
uspto-grants-1977_10
Patent number
US04055654

Reaction notes

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