Benzyl Bromide → 2-Phenylmethoxy-3-phenylmethylbenzaldehyde

HRID 2371435Notes

Reaction equation

HRID 2371435 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7]C2C(O)=CC=CC=2)=[CH:3][CH:2]=1.[C:15]1([CH2:21][C:22]2[CH:29]=[CH:28][CH:27]=[C:24]([CH:25]=[O:26])[C:23]=2[OH:30])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Br)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:4]1([CH2:7][O:30][C:23]2[C:22]([CH2:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:29][CH:28]=[CH:27][C:24]=2[CH:25]=[O:26])[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 242162-BenzylphenolHCID 222635343-(Phenylmethyl)salicylaldehyde

Product 1

HCID 199072502-Phenylmethoxy-3-phenylmethylbenzaldehydeYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Using the method of Tramposch, Kung and Blau (J. Med. Chem. (1983) 26, 121), 2-hydroxydiphenylmethane was converted to 3-(phenylmethyl)salicylaldehyde in 56% yield: NMR (CDCl3) 11.35 (s, 1H), 9.35 (s, 1H), 7.45-6.85 (m, 8H), 4.00 (s, 2H); Mass spec (CI) 213. This hydroxyaldehyde (31.3 g, 0.147 mole) was treated with benzyl bromide (25.2 g, 0.147 mole) and potassium carbonate (22.1 g, 0.16 mole) in N,N-dimethylformamide (180 mL) at 100° overnight. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Distillation of the residue (170°-185°, 0.1 torr) provided the title material as a pale yellow viscous oil in 71% yield. NMR (CDCl3) 10.3 (s, 1H), 7.8-7.1 (m, 13H), 4.9 (s, 2H), 4.05 (s, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationDistillation of the residue (170°-185°, 0.1 torr)

Sources & evidence

ORD record
ord-6b152517b4eb4d1898eb96516b907641
Source dataset
uspto-grants-1992_03
Patent number
US05093351

Reaction notes

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