Ethanol → HCID 20211033, compound

HRID 1906894Notes

Reaction equation

HRID 1906894 reaction equation
[CH3:1][C:2]1([C:13]([OH:15])=[O:14])[CH2:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH3:1][C:2]1([C:13]([O:15][CH2:21][CH3:22])=[O:14])[CH2:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 16643052HCID 16643052, compound

Product 1

HCID 20211033HCID 20211033, compoundYield 72.7%

Procedure

A mixture of 152 parts of 3,4-dihydro-2-methyl-4-oxo-2H-1-benzopyran-2-carboxylic acid, 18.4 parts of concentrate sulfuric acid and 2720 parts of ethanol was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in a mixture of 1,1'-oxybisethane and a sodium hydroxide solution. The organic layer was separated, washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 126 parts (72.7%) of ethyl 3,4-dihydro-2-methyl-4-oxo-2H-1-benzopyran-2-carboxylate as a residue (intermediate 26).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionthe residue was taken up in a mixture of 1,1'-oxybisethane
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-bb663b3f32524fedae9be5085427d10e
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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