Water → Phenol, 2,3-dimethyl-4-(phenylmethoxy)-

HRID 2102989Notes

Reaction equation

HRID 2102989 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[K+].[K+].[OH2:15]>CN(C=O)C>[CH2:1]([O:15][C:3]1[CH:4]=[CH:5][C:9]([OH:12])=[C:7]([CH3:6])[C:2]=1[CH3:1])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 23290216Phenol, 2,3-dimethyl-4-(phenylmethoxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,3-dimethyl-1,4-dihydroquinone (5 g) and benzyl bromide (6.2 g) and K2CO3 (10 g) in DMF (50 mL) was stirred at 120° C. for 5 h. The mixture was poured into water and extracted with EtOAc. The EtOAc was washed with water, dried and evaporated. The residue was purified by silica gel column eluting with 10% EtOAc in hexane to give 3.2 g of 4-benzyloxy-2,3-dimethyl-phenol as a pale solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc was washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-843271ad65f94a439d31ea758f985c97
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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