4-Benzylphenol → HCID 15006941, compound

HRID 1645892Notes

Reaction equation

HRID 1645892 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 75634-BenzylphenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 748286-Chloro-1-hexanol

Product 1

HCID 15006941HCID 15006941, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 40.0 g (0.217 mole) of p-benzylphenol (Eastman) and 29.7 g (0.217 mole) of 6-chlorohexan-1-ol (MCB) in 500 ml of dry dimethylformamide is stirred and heated to about 100° C., after which 33.1 g (0.24 mole) of potassium carbonate is added, and the mixture refluxed for 2.5 hours. The mixture is cooled, poured into ice-water, and 50 ml of 10% NaOH is added. The mixture is extracted with ether, the ether extracts washed with water and brine, dried (Mg2SO4), and the ether evaporated. The resultant oil is redistilled to give the product as a water-white oil fraction distilling at 140-175° C., 0.05 mmHg.

Workup

  1. temperaturethe mixture refluxed for 2.5 hours
  2. temperatureThe mixture is cooled
  3. additionis added
  4. extractionThe mixture is extracted with ether
  5. washthe ether extracts washed with water and brine
  6. dry with materialdried (Mg2SO4)
  7. customthe ether evaporated
  8. distillationThe resultant oil is redistilled
  9. customto give the product as a water-white oil fraction
  10. distillationdistilling at 140-175° C.

Sources & evidence

ORD record
ord-2c956414b9fd49caaa8b03e4591aadc7
Source dataset
uspto-grants-1993_01
Patent number
US05177108

Reaction notes

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