Ethanol → HCID 20211053, compound

HRID 1870985Notes

Reaction equation

HRID 1870985 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4][C:3]2[CH:10]=[CH:11][C:12]3[C:17]([C:2]1=2)=[CH:16][CH:15]=[CH:14][CH:13]=3.S(=O)(=O)(O)O.[CH2:23](O)[CH3:24]>>[O:1]1[CH:6]([C:7]([O:9][CH2:23][CH3:24])=[O:8])[CH2:5][CH2:4][C:3]2[CH:10]=[CH:11][C:12]3[C:17]([C:2]1=2)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 202110393,4-Dihydro-2H-naphtho[1,2-b]pyran-2-carboxylic acid

Product 1

HCID 20211053HCID 20211053, compoundYield 63.5%

Procedure

A mixture of intermediate (9-a) (7 g), ethanol (160 ml) and sulfuric acid was stirred and refluxed for 1 hour. The reaction mixture was evaporated and the oily residue was taken up in water. After treating with sodium hydroxide, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 5 g (63.5%) of ethyl 3,4dihydro-2H-naphto[1,2-b]pyran-2-carboxylate (interm. 10-a).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe reaction mixture was evaporated
  3. additionAfter treating with sodium hydroxide
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8a80dc99194f4682ab828f2959df70cb
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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