Tert-Butylhydroquinone → HCID 14746278, compound

HRID 2107361Notes

Reaction equation

HRID 2107361 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13](O)[CH3:14])[CH:5]=[C:6]([Br:12])[C:7]=1[O:8][C:9](=[O:11])[CH3:10].S([O-])(O)(=O)=O.[K+].C(C1C=C(O)C=CC=1O)(C)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:12])[C:7]=1[O:8][C:9](=[O:11])[CH3:10])[CH:13]=[CH2:14]

Participants

4

Reactant 3

HCID 16043Tert-ButylhydroquinoneHCID 516920Potassium bisulfateHCID 14746277HCID 14746277, compound

Product 1

HCID 14746278HCID 14746278, compound

Procedure

A mixture of 67.6 g (0.02 mole) 1-(3',5'-dibromo-4'-acetoxyphenyl)ethanol, 0.35 g freshly melted and then finely pulverized potassium hydrogen sulfate, and 0.5 g t-butylhydroquinone are heated at 20 Torr to 170°-190° C. The resulting product is distilled off (under vacuum) at a temperature of 140° to 160° C. It is taken up in ether, the ether solution is washed with Na2CO3, dried, and concentrated under vacuum. The remaining product is distilled at 0.02 mbar; the boiling point is 116° C. The isolated product, which is a highly viscous oil or a white, waxy solid, has a melting point of approximately 75° C. The reaction yield is 27 g.

Workup

  1. distillationThe resulting product is distilled off (under vacuum) at a temperature of 140° to 160° C
  2. washthe ether solution is washed with Na2CO3
  3. customdried
  4. concentrationconcentrated under vacuum
  5. distillationThe remaining product is distilled at 0.02 mbar
  6. customThe reaction yield is 27 g

Sources & evidence

ORD record
ord-4e22aa0e319d4d37a857768d85aa2759
Source dataset
uspto-grants-1990_06
Patent number
US04933495

Reaction notes

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