Hydroquinone → 4-(3-Bromopropoxy)phenol

HRID 839667Notes

Reaction equation

HRID 839667 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[Br:9][CH2:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:9][CH2:10][CH2:11][CH2:12][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate

Product 1

HCID 124399004-(3-Bromopropoxy)phenol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 88.0 g. (0.80 m.) of hydroquinone, 161.6 g. (0.80 m.) of 1,3-dibromopropane and 55.2 g. (0.40 m.) of potassium carbonate in 2 liters of 2-butanone was heated at reflux for 24 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo. The solid and liquid phases of the residue were separated, and the liquid fraction was chromatographed on silica gel using chloroform-acetonitrile (95:5) as the eluant. There was thus obtained 37.2 g. of 4-(3-bromopropyloxy)phenol as a light brown oil which was used directly in the next reaction.

Workup

  1. additionA mixture of 88.0 g
  2. temperatureat reflux for 24 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe solid and liquid phases of the residue were separated
  6. customthe liquid fraction was chromatographed on silica gel
  7. customof 4-(3-bromopropyloxy)phenol as a light brown oil which was used directly in the next reaction

Sources & evidence

ORD record
ord-23bd87595a53454f8e2b7128ace45f69
Source dataset
uspto-grants-1978_06
Patent number
US04096280

Reaction notes

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