Water → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 413789

反応式

HRID 413789 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[O:15])[C:12]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH2:1]([O:19][C:12]1[C:11]([O:10][CH3:9])=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

生成物 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehyde収率 81%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Benzyl bromide (8.6 ml) was added to a stirred solution of 3-methoxysalicylaldehyde (10 g), potassium carbonate (14.76 g) and potassium iodide (0.12 g) in DMF (120 ml) under an atmosphere of argon. The reaction was heated at 70° C. for 16 hours. Water (200 ml) was added causing the precipitation of a brown oil which crystallised on cooling. The solid was filtered, washed with water, dissolved in dichloromethane and dried (MgSO4). The solvent was removed in vacuo to give an oil which crystallised on trituration with iso-hexane to give the product as an off white solid (12.85 g, 81%); NMR d (CD3SOCD3) 3.91 (s, 3H), 5.15 (s, 2H), 7.14-7.22 (m, 2H), 7.29-7.42 (m, 6H), 10.10 (t, 1H); M/z (+) 243 (MH+).

後処理

  1. customthe precipitation of a brown oil which
  2. customcrystallised
  3. temperatureon cooling
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give an oil which
  10. customcrystallised on trituration with iso-hexane

出典と根拠

ORDレコード
ord-85cf6ef0ec784178b2581fde72b3ab84
出典データセット
uspto-grants-2003_05
特許番号
US06569888B1

関連ノート

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