Dihydrocoumarin → Methyl 3-(2-hydroxyphenyl)propionate

HRID 40819

Reaction equation

HRID 40819 reaction equation
[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]

Participants

6

Reactant 4

HCID 660DihydrocoumarinHCID 887MethanolHCID 1118Sulfuric AcidHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

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),

Workup

  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)

Sources & evidence

ORD record
ord-0d1a23406a3e491fad5f5e447a8bab4d
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Linked notes

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