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

HRID 254852

반응식

HRID 254852 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 3283Diethyl Ether용매

실험 절차

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, 3′-1).

후처리

  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

출처 및 근거

ORD 기록
ord-82484b72cc1544b1acaafd555bf77f32
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875726B2

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