Water → 2-(4-Ethylbenzyl)phenol

HRID 1182030Notes

Reaction equation

HRID 1182030 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]C)=[CH:5][CH:4]=1)[CH3:2].B(Br)(Br)Br.O>ClCCl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 17964392(4-Ethylphenyl)(2-methoxyphenyl)methane

Product 1

HCID 116585572-(4-Ethylbenzyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.83 g of (4-ethylphenyl)(2-methoxyphenyl)methane 55 is dissolved in dichloromethane. 11.0 ml of boron tribromide (1 M in CH2Cl2) are added dropwise to the mixture. The mixture is stirred at room temperature for 5 hours and, after addition of water, the dichloromethane phase is separated off. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water and NaCl solution, dried over sodium sulfate and concentrated. 0.77 g is obtained as crude product which can be purified by chromatography. C15H16O (212.29) MS (ESI): 235.20 (M+Na+)

Workup

  1. customthe dichloromethane phase is separated off
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washThe combined organic phases are washed with water and NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custom0.77 g is obtained as crude product which
  7. customcan be purified by chromatography

Sources & evidence

ORD record
ord-beda1aab79724a5890a4e1c56d86d2e5
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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