Ethanol → HCID 20211053, compound

HRID 399911Notes

Reaction equation

HRID 399911 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 3,4-dihydro-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-b0ce20378dc74282aaa65ede9c40900a
Source dataset
uspto-grants-1998_10
Patent number
US05824682

Reaction notes

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