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

HRID 1950089Notes

Reaction equation

HRID 1950089 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-oneYield 75.1%

Conditions

Temperature
100 °C

Procedure

The title compound was synthesized by referring to Chem. Pharm. Bull., 1977, 25, 2788. To 3-methoxyphenol (8.5 g) and 3,3-dimethylacrylic acid (7.5 g) was added polyphosphoric acid (80 ml), and the solution was stirred for 2 hours at 100° C. The reaction mixture was poured into an ice water, the solution was stirred, and then extracted with diethyl ether, then sequentially washed with an aqueous solution of 2N sodium hydroxide, water and brine, dried over anhydrous magnesium sulfate, then filtered through NH silica gel, and the solvent was evaporated in vacuo. The residue was washed with a hexane-diethyl ether system to provide the title compound (10.6 g).

Workup

  1. customThe title compound was synthesized
  2. stirringthe solution was stirred
  3. extractionextracted with diethyl ether
  4. washsequentially washed with an aqueous solution of 2N sodium hydroxide, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered through NH silica gel
  7. customthe solvent was evaporated in vacuo
  8. washThe residue was washed with a hexane-diethyl ether system

Sources & evidence

ORD record
ord-b3ee5fba4eed4ffd883f4d380a13ea33
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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