Sodium Hydroxide → HCID 14820112, compound

HRID 487078Notes

Reaction equation

HRID 487078 reaction equation
[C:1]([C:4]1[C:20]([OH:21])=[CH:19][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]#[N:16])=[C:6]([CH2:22][CH3:23])[CH:5]=1)(=[O:3])[CH3:2].[OH-:24].[Na+]>C(O)C>[C:1]([C:4]1[C:20]([OH:21])=[CH:19][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:17])([CH3:18])[C:15]([NH2:16])=[O:24])=[C:6]([CH2:22][CH3:23])[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14820102HCID 14820102, compound

Product 1

HCID 14820112HCID 14820112, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg of 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-2,2-dimethylheptanenitrile in 150 ml of 5N sodium hydroxide and 50 ml of ethanol was heated at reflux overnight. The ethanol was removed by evaporation, 100 ml of water were added, and the solution was extracted with diethyl ether. The organic layer was separated, dried, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane to provide 34 mg of the desired title product, m.p.=73°-74° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe ethanol was removed by evaporation, 100 ml of water
  4. additionwere added
  5. extractionthe solution was extracted with diethyl ether
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative thin layer chromatography over silica gel eluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-dba9062a3b4646c3988cee838954669b
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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