Hydroquinone → HCID 43143362, compound

HRID 853142Notes

Reaction equation

HRID 853142 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromide

Product 1

HCID 43143362HCID 43143362, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 10 g of hydroquinone in 90 ml of acetonitrile was treated with 8.58 g of 4-fluorobenzylbromide and 15.7 g of potassium carbonate. The mixture was heated to 90° C. and stirred during 18 h. For the working-up, the reaction mixture was cooled to room temperature and treated with cold water. The solid material that has formed was filtered, washed twice with cold water and dried. For purification and separation from the bis-ether, the crude material was chromatographed on silica gel using a 4:1 mixture of heptane and ethyl acetate as the eluent. There were obtained 4.05 g (27% of theory) of 4-(4-fluoro-benzyloxy)-phenol as a white solid; MS: m/e=218 (M)+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe solid material that has formed
  3. filtrationwas filtered
  4. washwashed twice with cold water
  5. customdried
  6. customFor purification and separation from the bis-ether
  7. customthe crude material was chromatographed on silica gel using
  8. additiona 4:1 mixture of heptane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-7787e7ea6ce74438867ca09f3df85980
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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