Methanol → HCID 20211027, compound

HRID 1906878Notes

Reaction equation

HRID 1906878 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:5]=2[O:4]1.[CH3:16]O>S(=O)(=O)(O)O>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][C:5]=2[O:4]1

Participants

4

Reactant 2

HCID 887MethanolHCID 20211048HCID 20211048, compound

Product 1

HCID 20211027HCID 20211027, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a stirred solution of 40 parts of 3,4-dihydro-2-(hydroxymethyl)-2H-1-benzopyran-6-carboxylic acid in 400 parts of methanol were added a few drops of sulfuric acid. Stirring was continued overnight at reflux. The reaction mixture was evaporated. The residue was taken up in 1,1'-oxybisethane. The whole was washed with a sodium hydroxide solution 10% and with water, dried, filtered and evaporated, yielding 24 parts (53.9%) of methyl 3,4-dihydro-2-(hydroxymethyl)-2H-1-benzopyran-6-carboxylate as a residue (intermediate 4).

Workup

  1. temperatureat reflux
  2. customThe reaction mixture was evaporated
  3. washThe whole was washed with a sodium hydroxide solution 10% and with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-baf1cf20f99b4b5db32f6c82bac56256
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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