Salicyl Alcohol → Benzenemethanol, 2-butoxy- (9CI)

HRID 2243285Notes

Reaction equation

HRID 2243285 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH3:4].[OH:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10].C(=O)([O-])[O-].[K+].[K+]>CC(O)C.C(OCC)(=O)C>[CH2:1]([O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][OH:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 5146Salicyl AlcoholHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 23014Benzenemethanol, 2-butoxy- (9CI)

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

12.4 g (90.5 mmol) of butyl bromide, 11.2 g (90.5 mmol) of 2-hydroxybenzyl alcohol and 12.5 g (90.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate and washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe suspension is cooled
  3. washwashed with 1N aqueous sodium hydroxide solution and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d220ddda343e49faaf2c31c013f9b97f
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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