Dihydrocoumarin → Methyl 3-(2-hydroxyphenyl)propionate

HRID 40819

반응식

HRID 40819 반응식
[CH:1]1[CH:2]=[CH:3][C:4]2[O:11][C:9](=[O:10])[CH2:8][CH2:7][C:5]=2[CH:6]=1.OS(O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:23][OH:24]>O>[OH:24][C:23]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH2:7][CH2:8][C:9]([O:11][CH3:4])=[O:10]

참가 물질

6

반응물 4

HCID 660DihydrocoumarinHCID 887MethanolHCID 1118Sulfuric AcidHCID 11430Potassium Carbonate

생성물 1

HCID 2794569Methyl 3-(2-hydroxyphenyl)propionate수율 90%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

To a stirred solution of dihydrocoumarin (10 mL, 78.9 mmol) and a catalytic amount of conc. H2SO4 in dry methanol (300 mL) was added and the reaction mixture was then heated at 55° C. for 8 hours. Methanol was evaporated to dryness to give crude product which was subjected to neutralize with K2CO3. The residue was diluted with water and extracted with dichloromethane. Purification of the crude product by column chromatography (20% CH2Cl2:3% EtOAc:77% Hexane as eluent) gave the desired ester as colorless oil (12.80 g, 90%). 1H NMR (400 MHz, CDCl3): 2.71 (3H, t, J=6.4 Hz), 2.89 (2H, t, J=6.4 Hz), 3.67 (3H, s), 6.83-6.87 (2H, m), 7.06-7.12 (2H, m),

후처리

  1. customMethanol was evaporated to dryness
  2. customto give crude product which
  3. extractionextracted with dichloromethane
  4. customPurification of the crude product by column chromatography (20% CH2Cl2:3% EtOAc:77% Hexane as eluent)

출처 및 근거

ORD 기록
ord-0d1a23406a3e491fad5f5e447a8bab4d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530491B2

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