Ethanol → HCID 20211023, compound

HRID 1906898Notes

Reaction equation

HRID 1906898 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[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[C:2]1=2.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[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=3[C:2]1=2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20211041HCID 20211041, compound

Product 1

HCID 20211023HCID 20211023, compoundYield 100%

Procedure

A mixture of 20 parts of 3,4,7,8,9,10-hexahydro-2H-naphtho[1,2-b]pyran-2-carboxylic acid, 200 parts of ethanol and 4.6 parts of sulfuric acid was stirred and refluxed for 2 hours. The reaction mixture was evaporated. Water and a sodium hydroxide solution were added to the residue. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated, yielding 21 parts (100%) of ethyl 3,4,7,8,9,10-hexahydro-2H-naphtho[1,2-b]pyran-2-carboxylate as a residue (intermediate 30).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture was evaporated
  3. additionWater and a sodium hydroxide solution were added to the residue
  4. extractionThe product was extracted with dichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-58855f107b4149969a8e33aac9160ab7
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

Loading…