Salicyl Alcohol → [2-(5-Phenylpentyloxy)phenyl]methanol

HRID 1672628Notes

Reaction equation

HRID 1672628 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5146Salicyl AlcoholHCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzene

Product 1

HCID 20764199[2-(5-Phenylpentyloxy)phenyl]methanolYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 10 g (80.56 mmol) of 2-hydroxybenzyl alcohol in 200 ml of dry acetonitrile is mixed with 27.45 g (120.83 mmol) of (5-bromopentyl)benzene from Example 26A and 12.25 g (88.61 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 18.7 g (81% yield) of a colorless solid are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting organic phase is concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-8bf299b9ffcc406385bf79b97ae39af4
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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