Benzyl Chloride → 1-Benzyloxy-2-tert-butyl-4-methyl-benzene

HRID 19779

Reaction equation

HRID 19779 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:12][C:6]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 170042-tert-Butyl-4-methylphenol

Product 1

HCID 508863431-Benzyloxy-2-tert-butyl-4-methyl-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8 g of 2-tert-Butyl-4-methyl-phenol (49 mmol) and 16.36 g of potassium carbonate (58 mmol) were stirred in 120 ml DMF until a suspension was formed. 6.74 ml of benzylchloride were then added dropwise and the reaction mixture was stirred for 24 h at RT. After two hours heating at 60° C., the reaction mixture was cooled to RT, filtered off, diluted with ethyl acetate, and washed with water followed by brine. The organic phase was dried over magnesium sulphate, filtered off and concentrated under vacuo. The residue was purified by flash column chromatography (heptane/AcOEt 98/2) to give 8.647 g of a colorless liquid. MS (ISP) 255.3 (M+H)+.

Workup

  1. customwas formed
  2. temperatureAfter two hours heating at 60° C.
  3. temperaturethe reaction mixture was cooled to RT
  4. filtrationfiltered off
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic phase was dried over magnesium sulphate
  8. filtrationfiltered off
  9. concentrationconcentrated under vacuo
  10. customThe residue was purified by flash column chromatography (heptane/AcOEt 98/2)

Sources & evidence

ORD record
ord-8cdae5bcb04442f4acfe2417bcb9c0c9
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Linked notes

Loading…