Sodium Hydroxide → HCID 20475020, compound

HRID 2295257Notes

Reaction equation

HRID 2295257 reaction equation
[CH2:1]([CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C(=O)C)[CH:14]=1)[C:10]([NH2:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>CO>[CH2:1]([CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)[C:10]([NH2:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20475016HCID 20475016, compound

Product 1

HCID 20475020HCID 20475020, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a chilled solution of 10.14 g of the mixture containing octyl 3-acetoxyphenylacetamide and 100 ml of methanol was added 12.63 ml of 5 N NaOH. The mixture was stirred at room temperature for 3 hours after which the methanol was removed in vacuuo. The residue was dissolved in 100 ml of 1 N NaOH and extracted with 50 ml of ether. The resulting aqueous phase was acidified with conc. hydrochloric acid and extracted twice with 100 ml of ether. The combined ether extracts were washed with 75 ml of water and 75 ml of brine, dried (MgSO4), filtered, and evaporated to provide 7.55 g of crude product which was recrystallized from toluene-pentane to yield 5.03 g of octyl 3-hydroxyphenylacetamide, m.p. 60°-62° C. Anal. Calc'd for C16H25NO2 : C, 73.00; H, 9.58; N, 5.32. Found: C, 72.86; H, 9.63; N, 5.16.

Workup

  1. customwas removed in vacuuo
  2. dissolutionThe residue was dissolved in 100 ml of 1 N NaOH
  3. extractionextracted with 50 ml of ether
  4. extractionextracted twice with 100 ml of ether
  5. washThe combined ether extracts were washed with 75 ml of water and 75 ml of brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto provide 7.55 g of crude product which
  10. customwas recrystallized from toluene-pentane

Sources & evidence

ORD record
ord-113be1d2ef664a29975e049a045d1841
Source dataset
uspto-grants-1984_01
Patent number
US04424205

Reaction notes

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