Dimethylformamide → HCID 18979151, compound

HRID 2393188Notes

Reaction equation

HRID 2393188 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:27]([CH3:28])=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[O:29][CH3:30])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:4][CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[CH3:31][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[C:27]([CH3:28])=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[O:29][CH3:30])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18979232HCID 18979232, compound

Product 1

HCID 18979151HCID 18979151, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 6-(4-hydroxyphenyl)-6-(l-methoxy-3-methylnaphth-2-yl)hexanoate (30 g) was stirred with potassium carbonate (90 g), iodomethane (45 ml), and DMF (150 ml) overnight at ambient temperature. The reaction mixture was poured into cooled water and extracted with IPE. The organic layer was washed with water, dried, and evaporated. The residue was dissolved in ethanol (250 ml) and refluxed with 2.5N sodium hydroxide (250 ml) for 5 hours. Ethanol was removed and the residue was acidified with conc.HCl and extracted with ethyl acetate. The organic layer was washed with water, dried, and evaporated to give the titled compound (25 g) as crude oil.

Workup

  1. additionThe reaction mixture was poured
  2. extractionextracted with IPE
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. dissolutionThe residue was dissolved in ethanol (250 ml)
  7. temperaturerefluxed with 2.5N sodium hydroxide (250 ml) for 5 hours
  8. customEthanol was removed
  9. extractionHCl and extracted with ethyl acetate
  10. washThe organic layer was washed with water
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-759de72dc7434c6f9e0c902b0394e3f7
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

Loading…