Methanol → HCID 59568776, compound

HRID 1643302Notes

Reaction equation

HRID 1643302 reaction equation
[CH3:1][O:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].OS(O)(=O)=O.[CH3:21]O>>[CH3:21][O:7][C:6](=[O:8])[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 59568814HCID 59568814, compound

Product 1

HCID 59568776HCID 59568776, compound

Procedure

To a solution of the 4-methoxy-4-o-tolyl-butyric acid obtained above in 6 mL methanol was added 60 μL concentrated H2SO4 at room temperature. After stirring for 12 h the reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×10 mL) and dried over Na2SO4. The product was isolated by flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give 229 mg of the title compound as an oil.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  4. washThe combined organic layers were washed with brine (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. customThe product was isolated by flash column chromatography
  7. washeluting with 0% to 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7af150efc5754c95ad7ddb2b50cffc7d
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

Loading…