tert-Butylcatechol → HCID 14746275, compound

HRID 1742799Notes

Reaction equation

HRID 1742799 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13](O)[CH3:14])[CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][C:9](=[O:11])[CH3:10].OS([O-])(=O)=O.[K+].C(C1C=CC=C(O)C=1O)(C)(C)C>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][C:9](=[O:11])[CH3:10])[CH:13]=[CH2:14]

Participants

4

Reactant 3

HCID 77643tert-ButylcatecholHCID 516920Potassium bisulfateHCID 14746274HCID 14746274, compound2×

Product 1

HCID 14746275HCID 14746275, compoundYield 81.8%

Conditions

Temperature
187.5 °C

Procedure

(36.6 g, 0.30 mol) of 2,6-dimethylphenol are mixed in an Hastelloy C autoclave with 0.315 mol of acetic anhydride and 9 mols of hydrogen flouride. The temperature is raised to 50° C. and the reaction runs for 3 hours. After extraction and wash, 47.4 g of a gray to purple solid mass of 3,5-dimethyl4-hydroxyacetophenone is obtained. This solid is then esterified by refluxing with 4 mols of acetic anhydride for 19 hours. After removal of acetic acid and acetic anhydride by vacuum distillation the 3,5-dimethyl-4-acetoxyacetophenone is flash distilled to yield 47.7 g of a slightly yellow liquid. 0.1 mol of the 3,5-dimethyl-4-acetoxyacetophenone, 1.2 g of 5% Pd/C as catalyst and 100 ml ethanol are mixed in an autoclave and the autoclave is charged with hydrogen gas at a pressure of 215-220 mm Hg and the reaction is run for about 21/2 hours at a temperature of about 25°-30° C. Additional catalyst is added as needed. The catalyst is then removed and the ethanol evaporated to yield 21.5 g of a colorless oil which is (3,5-dimethyl-4-acetoxyphenyl)ethanol. 0.168 mol of (3,5-dimethyl-4-acetoxyphenyl)ethanol is added to a flask with 0.35 g KHSO4 and 0.5 g t-butyl catechol. The flask is heated to 185 to 190° C. at 1.5 to 2.0 mm Hg. A colorless liquid is distilled. After the addition of 0.15 g of t-butyl catechol, and redistillation, 26.1 g of 3,5- dimethyl-4-acetoxystyrene monomer is produced. The compound has a boiling point of 90°-91° C. at 0.5 mm of Hg and the yield is 81.8%.

Workup

  1. distillationA colorless liquid is distilled
  2. additionAfter the addition of 0.15 g of t-butyl catechol, and redistillation

Sources & evidence

ORD record
ord-b5e3a58038764e2b907719aef26ea352
Source dataset
uspto-grants-1994_08
Patent number
US05342727

Reaction notes

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