Methanol → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

HRID 1662371Notes

Reaction equation

HRID 1662371 reaction equation
[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:21]O>>[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([O:8][CH3:21])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

Product 1

HCID 57706598Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

Procedure

To a flask containing 3-cyclopropyl-3-(3-hydroxyphenyl)propanoic acid 66.6V (1.2 g, 5.8 mmol) in MeOH (15 mL) was added H2SO4 (0.31 mL, 5.8 mmol). The resulting mixture was stirred at reflux overnight. The reaction was concentrated and purified by combiflash chromatography (0 to 30% EtOAc/Hexanes) to provide methyl 3-cyclopropyl-3-(3-hydroxyphenyl)propanoate 66.6W (1.2 g, 94%). Chiral separation was accomplished on Chiracel-OD (3% IPA in hexane) to provide 66.6X and 66.6Y. Peak 1 was the desired enantiomer. Analytical column (Chiracel-OD (2% IPA in hexane-45 min run) Peak 1-22.5 mins, Peak 2-34.0 mins).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated
  3. custompurified by combiflash chromatography (0 to 30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f0bc6f5db7a84cecaea3420fcb5e68e6
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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