Vanillin → 2-(4-Formyl-2-methoxyphenoxy)ethyl acetate

HRID 1865332

反応式

HRID 1865332 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[K+].[K+].[C:18]([O:21][CH2:22][CH2:23]Br)(=[O:20])[CH3:19]>CC(C)=O.C(OCC)C>[C:18]([O:21][CH2:22][CH2:23][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11])(=[O:20])[CH3:19]

参加物

6

反応物 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane

生成物 1

HCID 21704232-(4-Formyl-2-methoxyphenoxy)ethyl acetate収率 75.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 4-hydroxy-3-methoxy-benzaldehyde (2.5 g, 16.4 mmol), K2CO3 (6.81 g, 49.3 mmol) and 2-bromoethyl acetate (5.49 g, 32.9 mmol) in acetone (50 mL) is refluxed for 48 h before it is diluted with diethyl ether (250 mL) and washed with water (2×200 mL). The washings are extracted with diethyl ether (200 mL). The combined organic extracts are dried over MgSO4 and concentrated. The remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1 to afford the title compound (2.94 g) as colourless solid. 1H NMR (CDCl3): δ 9.85 (s, 1H), 7.45-7.41 (m, 2H), 6.99 (d, J=7.6 Hz, 1H), 4.51-4.47 (m, 2H), 4.34-4.30 (m, 2H), 3.94 (s, 3H), 2.11 (s, 3H).

後処理

  1. temperatureis refluxed for 48 h before it
  2. washwashed with water (2×200 mL)
  3. extractionThe washings are extracted with diethyl ether (200 mL)
  4. dry with materialThe combined organic extracts are dried over MgSO4
  5. concentrationconcentrated
  6. customThe remaining residue is purified by column chromatography on silica gel eluting with heptane/EA 1:1

出典と根拠

ORDレコード
ord-1764a601e1644fe68aee5662423a6023
出典データセット
uspto-grants-2009_12
特許番号
US07626037B2

関連ノート

読み込み中…