Sodium Hydroxide → HCID 20475027, compound

HRID 2295255Notes

Reaction equation

HRID 2295255 reaction equation
[CH2:1]([CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C(=O)C)=[C:15]([O:23]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][C:16]([OH:19])=[C:15]([OH:23])[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 20475019HCID 20475019, compound

Product 1

HCID 20475027HCID 20475027, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a chilled solution of 16.88 g of the mixture containing octyl 3,4-diacetoxyphenylacetamide and 100 ml of methanol was added 16 ml of 5 N NaOH. The reaction mixture was stirred for two hours at room temperature. The methanol was removed on a rotary evaporator, the residue dissolved in 100 ml of 0.1 N NaOH and the solution extracted with 100 ml of ether. The resulting aqueous phase was acidified with conc. HCl and thrice extracted with 150 ml of ether. The combined ether extracts were washed with 100 ml H2O, dried (Na2SO4), filtered and evaporated to yield 8.91 g of crude product. This material was chromatographed on silica gel with 60% ethyl acetate/hexane and subsequently recrystallized from ether-pentane to yield 2.3 g of white crystalline octyl 3,4-dihydroxyphenylacetamide, mp. 83°-85° C. Anal. Calc'd for C16H25NO3 : C, 68.78; H, 9.02; N, 5.01. Found: C, 68.69; H, 9.08; N, 4.98.

Workup

  1. customThe methanol was removed on a rotary evaporator
  2. dissolutionthe residue dissolved in 100 ml of 0.1 N NaOH
  3. extractionthe solution extracted with 100 ml of ether
  4. extractionextracted with 150 ml of ether
  5. washThe combined ether extracts were washed with 100 ml H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto yield 8.91 g of crude product
  10. customThis material was chromatographed on silica gel with 60% ethyl acetate/hexane
  11. customsubsequently recrystallized from ether-pentane

Sources & evidence

ORD record
ord-3a0f668717914bffa08b24cb46a02410
Source dataset
uspto-grants-1984_01
Patent number
US04424205

Reaction notes

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