Acetic Acid → HCID 22096865, compound

HRID 1458690Notes

Reaction equation

HRID 1458690 reaction equation
[CH2:1]1[O:3][CH2:2]1.[NH2:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1.[C:17](O)(=[O:19])[CH3:18]>>[OH:19][CH2:17][CH2:18][N:4]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1)[CH2:2][CH2:1][OH:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6354Ethylene OxideHCID 6422115Methyl(4-aminophenoxy)acetate

Product 1

HCID 22096865HCID 22096865, compound

Procedure

Ethylene oxide (10 g; 227 mmol) was added under ice cooling to a solution of 4.0 g (22 mmol) of methyl 4-aminophenoxyacetate in 22 ml of 30% acetic acid. After the resultant mixture was stirred overnight at room temperature, nitrogen gas was bubbled to eliminate excess ethylene oxide. Subsequent to neutralization with sodium hydrogencarbonate, sodium chloride was added, followed by extraction with n-butanol. The extract was dried over magnesium sulfate and the solvent was distilled out. The residue was purified by chromatography on a silica gel column (chloroform/methanol=20/1), whereby 5.29 g of the title compound were obtained as a colorless oil (yield: 89%).

Workup

  1. customnitrogen gas was bubbled
  2. additionSubsequent to neutralization with sodium hydrogencarbonate, sodium chloride was added
  3. extractionfollowed by extraction with n-butanol
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent was distilled out
  6. customThe residue was purified by chromatography on a silica gel column (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-0a96843362f847229f98f89cf48b4427
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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