Methanol → 3-Benzyloxybenzaldehyde

HRID 25834

反応式

HRID 25834 の反応式
[CH2:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].C[OH:22].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH2:23]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH:1]=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1408973-Benzylphenol

生成物 1

HCID 743423-Benzyloxybenzaldehyde

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 3-hydroxylbenzaldehyde 31 (5.0 g, 40 mmol) and K2CO3 (27.2 g, 197 mmol) in 200 ml CHCl3: 100 ml MeOH was added benzylbromide (5.9 ml, 49 mmol). The suspension was refluxed under nitrogen overnight. The solvent was removed by evaporation and the resulting oil was taken up in DCM and washed with water and brine and dried (Na2SO4). The crude product was purified by column chromatography to yield the product as a viscous oil which solidified upon sitting (8.48 g, 40 mmol, 98%). m.p. 46°. 1H NMR (500 MHz, CDCl3) δ 9.97 (s, 1H), 7.48-7.25 (m, 9H), 5.13 (s, 2H). 13C NMR (125 MHz, CD3OD) δ 191.8, 159.2, 137.8, 136.3, 130.0, 128.6, 128.1, 127.5, 123.41, 121.9, 113.3, 70.0. HRMS (EI) m/e calcd for C14H12O2: 212.08373, found: 212.0827.

後処理

  1. temperatureThe suspension was refluxed under nitrogen overnight
  2. customThe solvent was removed by evaporation
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-56afacbd8edf4ddb94d3f3ca93a30eb6
出典データセット
uspto-grants-2005_02
特許番号
US06858600B2

関連ノート

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