Acetic Acid → 6-(4-Hydroxybutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 463063Notes

Reaction equation

HRID 463063 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:20][C:19](=[O:21])[O:18][CH2:17][C:16]=2[CH:22]=1)(=O)C.C(O)(=O)C>O.CO>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:20][C:19](=[O:21])[O:18][CH2:17][C:16]=2[CH:22]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 132604944-[(2-Oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)oxy]butyl acetate

Product 1

HCID 132605006-(4-Hydroxybutoxy)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 24 gm (0.6 mol) of sodium hydroxide in 100 ml of water is added dropwise to a solution of 150 gm (0.537 mol) of 6-(4-acetoxy-butoxy)-4H-3,1-benzoxazin-2-one in 500 ml of methanol, under stirring, at 10° to 15° C. After the mixture has been stirred for one hour at ambient temperature, first ice water and then 60 ml of glacial acetic acid are added. The product precipitated is subjected to suction filtration and recrystallized from water.

Workup

  1. stirringAfter the mixture has been stirred for one hour at ambient temperature
  2. customThe product precipitated
  3. filtrationis subjected to suction filtration
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-41316cb0b16a4fd8b9c2e9f043c7e06b
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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