Hydroquinone → HCID 178443562, compound

HRID 1090602Notes

Reaction equation

HRID 1090602 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]Br)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:16]1([CH:23]=[CH:22][C:20]([OH:21])=[CH:19][CH:18]=1)[OH:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:17][C:16]2[CH:23]=[CH:22][C:20]([OH:21])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 178443557HCID 178443557, compound

Product 1

HCID 178443562HCID 178443562, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g of (trans-4-heptylcyclohexyl)methyl bromide, 10.0 g of hydroquinone, 10.0 g of anhydrous potassium carbonate and 100 ml of absolute dimethylformamide was heated under reflux overnight. The cooled reaction mixture was subsequently poured into ice-water and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed with 500 ml of water, dried over magnesium sulphate and concentrated. Chromatography of the residue on silica gel with toluene/ethyl acetate (vol. 4:1) gave 1.8 g of 4-[(trans-4-heptylcyclohexyl)methoxy]phenol; m.p. 107°-108° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e8f17f1233d423cb73ecb3a6d4a19b0
Source dataset
uspto-grants-1992_01
Patent number
US05082589

Reaction notes

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