Dihydrocoumarin → Methyl 3-(2-hydroxyphenyl)propionate

HRID 40819

反応式

HRID 40819 の反応式
[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]

参加物

6

反応物 4

HCID 660DihydrocoumarinHCID 887MethanolHCID 1118Sulfuric AcidHCID 11430Potassium Carbonate

生成物 1

HCID 2794569Methyl 3-(2-hydroxyphenyl)propionate収率 90%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

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),

後処理

  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)

出典と根拠

ORDレコード
ord-0d1a23406a3e491fad5f5e447a8bab4d
出典データセット
uspto-grants-2013_09
特許番号
US08530491B2

関連ノート

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