Hydrochloric Acid → Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl ester

HRID 1461890Notes

Reaction equation

HRID 1461890 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:8]=[C:9](C(C)(C)C)[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Product 1

HCID 3084638Benzenepropanoic acid, 3-(1,1-dimethylethyl)-4-hydroxy-, methyl esterYield 71.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 50 g of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2.5 g of conc. hydrochloric acid and 30 ml of toluene was refluxed for 2 hours while stirring. After the completion of the reaction, the reaction mixture was washed with water and the solvent wa distilled off. Hexane was added to the residue and the mixture was icecooled. The resulting crystals were collected by filtration and recrystallized from hexane to give 29 g of methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate as white crystals, m.p. 59°-61° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed with water
  4. distillationthe solvent wa distilled off
  5. additionHexane was added to the residue
  6. filtrationThe resulting crystals were collected by filtration
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-f941720abb724c46ac78a04023a1f2e3
Source dataset
uspto-grants-1991_12
Patent number
US05077424

Reaction notes

Loading…