Hydroquinone → HCID 178444471, compound

HRID 2254992Notes

Reaction equation

HRID 2254992 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14]Br)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:16]1([CH:23]=[CH:22][C:20]([OH:21])=[CH:19][CH:18]=1)[OH:17].C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][O:17][C:16]2[CH:23]=[CH:22][C:20]([OH:21])=[CH:19][CH:18]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 178444432HCID 178444432, compound

Product 1

HCID 178444471HCID 178444471, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of 3-(trans-4-pentylcyclohexyl)-1-propyl bromide, 10.0 g of hydroquinone, 10.0 g of anhydrous potassium carbonate and 250 ml of absolute butanone was heated under reflux overnight. Subsequently, the cooled reaction mixture was poured into water and extracted three times with 100 ml of dichloromethane each time. The combined organic phases were washed with 500 ml of water, dried over magnesium sulfate, filtered and concentrated. Chromatography of the residue on silica gel with toluene/ethyl acetate (vol. 4:1) gave 2.9 g of 4-[3-(trans-4-pentylcyclohexyl)-1-propyloxy]phenol; m.p. 100°-101° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customSubsequently, the cooled reaction mixture
  4. extractionextracted three times with 100 ml of dichloromethane each time
  5. washThe combined organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4c09eeba853c4c40801d08f4dc2169a0
Source dataset
uspto-grants-1993_08
Patent number
US05238600

Reaction notes

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