Methanol → 4-Bromo-3-(hydroxymethyl)-2-propylphenol

HRID 552445Notes

Reaction equation

HRID 552445 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([CH2:10][CH2:11][CH3:12])=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.CO.[Br-:15].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:15][C:8]1[CH:7]=[CH:6][C:5]([OH:9])=[C:4]([CH2:10][CH2:11][CH3:12])[C:3]=1[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 23500184Tetra-n-butylammonium tribromideHCID 579008323-(Hydroxymethyl)-2-propylphenol

Product 1

HCID 579008284-Bromo-3-(hydroxymethyl)-2-propylphenolYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(hydroxymethyl)-2-propylphenol (1.05 g, 6.32 mmol) in dichloromethane (50 mL)-methanol (30 mL) mixtures, tetrabutylammonium tribromide (3.20 g, 6.64 mmol) was added at 0° C. The mixture was stirred at the same temperature for 1 hour. Solvent was evaporated under reduced pressure. The residue was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (1.04 g, 67%) was obtained as colorless crystalline powder.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. additionThe residue was added with water
  3. extractionextracted with ethyl acetate
  4. washSubsequently, the organic layer was washed with saturated saline
  5. customdried
  6. concentrationconcentrated in vacuum
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-36010b1af34249a0a4a818c1044ab1d7
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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