Benzyl Bromide → (4-(Benzyloxy)-2-methylphenyl)methanol

HRID 1946386Notes

Reaction equation

HRID 1946386 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[CH3:10].[OH-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C.ClCCl>[CH3:10][C:4]1[CH:5]=[C:6]([O:9][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 180080544-(Hydroxymethyl)-3-methylphenol

Product 1

HCID 23077848(4-(Benzyloxy)-2-methylphenyl)methanolYield 36.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(hydroxymethyl)-3-methylphenol (4.25 g, 30.8 mmol) in ethanol (90 ml) was added 2M aqueous sodium hydroxide (17 ml, 34 mmol) and then benzyl bromide (3.65 ml, 30.8 mmol, Aldrich). The pale yellow mixture was stirred at ambient temperature under nitrogen overnight. The solvent was removed in vacuo to leave an aqueous suspension. The residue was partitioned between dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase extracted with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave an orange oil. The residue was loaded in dichloromethane and purified on silica (100 g×3) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and the solvent evaporated in vacuo to give {2-methyl-4-[(phenylmethyl)oxy]phenyl}methanol (2.59 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customto leave an aqueous suspension
  3. customThe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with dichloromethane (50 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto leave an orange oil
  10. custompurified on silica (100 g×3)
  11. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cac267eb1b8d40c7950fa82cc5031c4e
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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