Benzyl Chloride → 4-(Benzyloxy)-3,5-dimethylbenzaldehyde

HRID 374295Notes

Reaction equation

HRID 374295 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:11])[C:2]=1[O:1][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeYield 88.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.6 g (30.6 mmol) of 4-hydroxy 3,5-dimethyl benzaldehyde (Example E), 4.4 g (35 mmol) of benzyl chloride and 4.8 g (35 mmol) of anhydrous potassium carbonate in 100 mL of acetonitrile, is stirred at reflux for 18 hours overnight. The reaction flask and the inorganic salts are washed with fresh acetonitrile and the solvent is removed on a rotary evaporator. A diethyl ether solution of the residue is washed with 2×25 mL of 1N potassium hydroxide solution, brine, dried (magnesium sulfate) and evaporated. Distillation through a short path apparatus affords 6.5 g of the title compound; bp 149°-152° C./0.50 mm (190°-195° C).

Workup

  1. temperatureat reflux for 18 hours overnight
  2. washThe reaction flask and the inorganic salts are washed with fresh acetonitrile
  3. customthe solvent is removed on a rotary evaporator
  4. washA diethyl ether solution of the residue is washed with 2×25 mL of 1N potassium hydroxide solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. distillationDistillation through a short path apparatus

Sources & evidence

ORD record
ord-e8261633d9204225bdfc53c3c680d4ed
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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