Acetone → HCID 57164035, compound

HRID 2231675Notes

Reaction equation

HRID 2231675 reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[OH:12])[CH2:2][CH2:3][CH3:4].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C1C=CC=CC=1.CCCCCC>[CH2:13]([O:12][C:6]1[CH:7]=[CH:8][C:9]([Br:11])=[CH:10][C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22134521HCID 22134521, compound

Product 1

HCID 57164035HCID 57164035, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 110624Benzene hexaneSolvent

Procedure

A mixture comprising 31.12 g of the above phenol, 18.81 g of benzyl bromide, 18.24 g of potassium carbonate and 300 ml of acetone, was stirred at room temperature for 2 days. Acetone was distilled off, and water was added to the residue. The mixture was extracted with benzene. The benzene layer was washed with a saturated sodium chloride aqueous solution, and dried over sodium sulfate. Then, the solvent was distilled off to obtain a pale yellow oily substance. This substance was subjected to silica gel column chromatography by using benzene-n-hexane (1:9, v/v) as the developer, whereby 30.07 g of (2-n-butyl-4-bromophenyl) benzyl ether was obtained as a colorless oily substance.

Workup

  1. distillationAcetone was distilled off
  2. additionwater was added to the residue
  3. extractionThe mixture was extracted with benzene
  4. washThe benzene layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over sodium sulfate
  6. distillationThen, the solvent was distilled off
  7. customto obtain a pale yellow oily substance

Sources & evidence

ORD record
ord-a2b01f774be549d4a001c2eceff0d5bf
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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