Potassium Carbonate → 4-(2-Acetoxy-ethoxy)-3-methylbenzaldehyde

HRID 38713

反応式

HRID 38713 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].[C:17]([O:20][CH2:21][CH2:22]Br)(=[O:19])[CH3:18]>CC(C)=O.C(OCC)C>[C:17]([O:20][CH2:21][CH2:22][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10])(=[O:19])[CH3:18]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 1399014-Hydroxy-3-methylbenzaldehyde

生成物 1

HCID 866118134-(2-Acetoxy-ethoxy)-3-methylbenzaldehyde収率 97.5%

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-methyl-benzaldehyde (7.0 g, 51.4 mmol), K2CO3 (21.32 g, 154.2 mmol) and 2-bromoethyl acetate (25.8 g, 154.2 mmol) in acetone (250 mL) is refluxed for 18 h before it is diluted with diethyl ether (300 mL) and washed with water (3×250 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 (11.14 g) as colourless solid. 1H NMR (CDCl3):δ 9.85 (s, 1H), 7.72-7.67 (m, 2H), 6.92-6.88 (m, 1H), 4.51-4.46 (m, 2H), 4.29-4.25 (m, 2H), 2.27 (s, 3H), 2.11 (s, 3H).

後処理

  1. temperatureis refluxed for 18 h before it
  2. washwashed with water (3×250 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-9998e3b1c06946889d0e0f9298ea029c
出典データセット
uspto-grants-2013_09
特許番号
US08524752B2

関連ノート

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