3-Methoxyphenol → 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 2180451Notes

Reaction equation

HRID 2180451 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11]([CH3:16])=[CH:12][C:13](O)=[O:14]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:10])[O:9]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 90073-MethoxyphenolHCID 109313-Methyl-2-butenoic acid

Product 1

HCID 6056607-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methoxyphenol (5.00 g, 40.3 mmol) and 3,3-dimethylacrylic acid (4.03 g, 40.3 mmol) were ground in a mortar. The mixture was then added portion-wise into polyphosphoric acid (8 g) at 90° C. After stirring at 90° C. for 30 min, the reaction mixture was quenched with ice, then extracted with diethyl ether. The organic layers were washed with water; brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo and purified by column chromatography (silica gel, 10% ethyl acetate in hexane) to give the title compound as a yellow solid.

Workup

  1. customthe reaction mixture was quenched with ice
  2. extractionextracted with diethyl ether
  3. washThe organic layers were washed with water
  4. dry with materialbrine, and dried over Na2SO4
  5. concentrationThe filtered solvent was concentrated in vacuo
  6. custompurified by column chromatography (silica gel, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c0f6966b0ada4ee5bfa713093ec46124
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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