Benzyl Chloride → 4-Benzyloxy-alpha-ethyldesoxybenzoin

HRID 1706166Notes

Reaction equation

HRID 1706166 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]([CH2:17][CH3:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.O.[I-].[K+]>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]([CH2:17][CH3:18])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:7]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 2272781-(4-Hydroxyphenyl)-2-phenylbutan-1-one

Product 1

HCID 189765134-Benzyloxy-alpha-ethyldesoxybenzoin

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-α-ethyldesoxybenzoin (44.5 g.), sodium carbonate (18.5 g.), potassium iodide (1.4 g.) and benzyl chloride (19 ml.) in ethanol (350 ml.) and water (50 ml.) was stirred and heated under reflux for 8 hours. The mixture was cooled, filtered and the residue washed with water to give 4-benzyloxy-α-ethyldesoxybenzoin (54.3 g.), m.p. 71° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe residue washed with water

Sources & evidence

ORD record
ord-528364d8dd7c4792bab41a8275fa4036
Source dataset
uspto-grants-1980_06
Patent number
US04206234

Reaction notes

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