Hydrochloric Acid → 2-tert-Butyl-4-methylphenyl prop-2-enoate

HRID 1719349Notes

Reaction equation

HRID 1719349 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)(=[O:16])[CH:14]=[CH2:15].Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:13]([O:12][C:6]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:16])[CH:14]=[CH2:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 202680562-tert-Butyl-4-methylphenyl prop-2-enoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent2×

Procedure

To a 300-ml four-necked flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel were added 32.8 g (0.20 mole) of 2-tert-butyl-4-methylphenol, 22.3 g (0.22 mole) of triethylamine and 100 g of toluene, and after replacing air in the flask by nitrogen, 19.10 g (0.21 mole) of acryloyl chloride was added dropwise at a reaction temperature of 30° C. over 1 hour. After completion of the dropwise addition, excessive triethylamine was neutralized with hydrochloric acid, the reaction solution was washed with water, and toluene was then removed from the organic layer by evaporation under reduced pressure to obtain 43.0 g of a crude product (yield, 99%). This crude product was purified by distillation under reduced pressure to obtain a white and transparent 2-tert-butyl-4-methylphenol monoacrylate.

Workup

  1. customTo a 300-ml four-necked flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel
  2. additionwas added dropwise at a reaction temperature of 30° C. over 1 hour
  3. washthe reaction solution was washed with water, and toluene
  4. customwas then removed from the organic layer by evaporation under reduced pressure
  5. customto obtain 43.0 g of a crude product (yield, 99%)
  6. distillationThis crude product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-824f1c3cfa8e48caaa2b8c9808dc05a3
Source dataset
uspto-grants-1985_09
Patent number
US04539355

Reaction notes

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