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

HRID 80007

반응식

HRID 80007 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 866118134-(2-Acetoxy-ethoxy)-3-methylbenzaldehyde수율 97.5%

시약·촉매·용매 2

HCID 180Acetone용매HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ebf380adaa2740bab63c180c3cafecf8
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045174E1

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