Sulfuric Acid → 2-methyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one

HRID 1448517Notes

Reaction equation

HRID 1448517 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:15][CH3:16])[C:13]=1[OH:14])[O:10][C:9](=[O:17])[CH:8]=[CH:7]2)[CH:2]=[CH2:3].S(=O)(=O)(O)O>>[CH3:3][CH:2]1[O:14][C:13]2=[C:12]([O:15][CH3:16])[C:11]3[O:10][C:9](=[O:17])[CH:8]=[CH:7][C:6]=3[CH:5]=[C:4]2[CH2:1]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 218145006-Allyl-7-hydroxy-8-methoxycoumarin

Product 1

HCID 203802232-methyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one

Procedure

A sample of 1.0 g. (4.31 mmoles) of 6-allyl-7-hydroxy-8-methoxycoumarin was dissolved in 20 ml. of conc. sulfuric acid at 25°. After 10 min, the solution was diluted with ice water. The mixture was extracted with methylene chloride, dried over sodium sulfate, and evaporated to yield 90 g. of residue. This was filtered through a column of silica gel, eluting with benzene/ethyl acetate, 4:1, to afford, upon evaporation of the filtrate, pure 2-methyl-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one as a white solid. Recrystallization from ethanol yielded an analytical sample, mp 115°-116°.

Workup

  1. customat 25°
  2. extractionThe mixture was extracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto yield 90 g
  6. filtrationThis was filtered through a column of silica gel
  7. washeluting with benzene/ethyl acetate, 4:1

Sources & evidence

ORD record
ord-3b7ed2c0dbc743299b6a029e4606b795
Source dataset
uspto-grants-1979_12
Patent number
US04180659

Reaction notes

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