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

HRID 2061278

反応式

HRID 2061278 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-fdbe5c553366419a9fa76c86b2f07559
出典データセット
uspto-grants-2012_10
特許番号
USRE043728E1

関連ノート

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