Hydroquinone → 4-(Cyclopropylmethoxy)phenol

HRID 979901Notes

Reaction equation

HRID 979901 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[Na+].[CH:11]1([CH2:14]Cl)[CH2:13][CH2:12]1.[I-].[K+]>O.C(O)(C)C>[CH:11]1([CH2:14][O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 80013(Chloromethyl)cyclopropane

Product 1

HCID 137554954-(Cyclopropylmethoxy)phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 11.0 g of hydroquinone, 80 ml of isopropanol, 4.1 g of sodium hydroxide in 4.5 ml water, 9.9 g of cyclopropylmethyl chloride and 0.5 g of potassium iodide is stirred under reflux for 12 hours. The solvent is evaporated and the residue is extracted with ether. The ether extract is washed successively with water, sodium bicarbonate solution, dilute sodium bisulfite solution, water and sodium chloride solution and dried. The crude product obtained after evaporation of solvent is purified by preparative chromatography on silica gel, using first toluene and then toluene-ethyl acetate (90:5 to 85:15) as eluent to yield p-(cyclopropylmethoxy)-phenol, m.p. 49°-52°.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe solvent is evaporated
  3. extractionthe residue is extracted with ether
  4. extractionThe ether extract
  5. washis washed successively with water, sodium bicarbonate solution, dilute sodium bisulfite solution, water and sodium chloride solution
  6. customdried
  7. customThe crude product obtained
  8. customafter evaporation of solvent
  9. customis purified by preparative chromatography on silica gel

Sources & evidence

ORD record
ord-4924c4d5df7441858ad40fabfcabf85a
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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