Benzyl Bromide → 2-Phenylmethoxy-3-phenylmethylbenzaldehyde

HRID 2371435ノート

反応式

HRID 2371435 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 199072502-Phenylmethoxy-3-phenylmethylbenzaldehyde収率 71%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6b152517b4eb4d1898eb96516b907641
出典データセット
uspto-grants-1992_03
特許番号
US05093351

反応ノート

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