Hydrochloric Acid → 2-tert-Butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate

HRID 638674Notes

Reaction equation

HRID 638674 reaction equation
[CH2:1]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]=1[OH:25])[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[C:26](Cl)(=[O:29])[CH:27]=[CH2:28].Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:26]([O:25][C:15]1[C:16]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13])(=[O:29])[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 13140Acryloyl chloride

Product 1

HCID 1090582-tert-Butyl-6-(3-tert-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylateYield 94.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent2×

Procedure

To a 500-ml four-necked flask equipped with a thermometer, stirring apparatus, condenser and dropping funnel were added 82.0 g (0.241 mole) of 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 200 g of toluene and 23.9 g (0.290 mole) of triethylamine. After replacing the air in the container with nitrogen, 25 g (0.276 mole) of acryloyl chloride was added dropwise with stirring. After completion of the dropwise addition, stirring was continued for 1 hour, excess triethylamine was neutralized with a dilute hydrochloric acid and the formed triethylamine hydrochloride was then removed by washing with water. Toluene was then removed by evaporation from the toluene layer after completion of the washing, and the residue obtained was recrystallized from 20 g of n-hexane to obtain 90.0 g of 2,2'-methylenebis(6-tert-butyl-4-methylphenol) monoacrylate as a white crystal. Melting point, 132°-134° C. Yield, 95%.

Workup

  1. customTo a 500-ml four-necked flask equipped with a thermometer
  2. additionwas added dropwise
  3. stirringwith stirring
  4. additionAfter completion of the dropwise addition
  5. stirringstirring
  6. customthe formed triethylamine hydrochloride was then removed
  7. washby washing with water
  8. customToluene was then removed by evaporation from the toluene layer after completion of the washing
  9. customthe residue obtained
  10. customwas recrystallized from 20 g of n-hexane

Sources & evidence

ORD record
ord-5c626098b6624ff5ab4929555e564683
Source dataset
uspto-grants-1985_12
Patent number
US04562281

Reaction notes

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