Hydrochloric Acid → 5-(Ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylic acid

HRID 1918528Notes

Reaction equation

HRID 1918528 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][CH:7]1[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH2:8]1)[CH3:4].Cl>C(O)C>[CH2:3]([O:5][CH2:6][CH:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH2:8]1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66831765HCID 66831765, compound

Product 1

HCID 668317425-(Ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1M solution of sodium hydroxide (5 mL; 5 mmol) was added to the solution of ethyl 5-(ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylate (0.135 g, 0.67 mmol) in ethanol (1 mL). The reaction mixture was stirred at room temperature overnight. The solution was acidified to pH 0-1 by addition of 6N hydrochloric acid and was extracted with ethyl acetate. Combined ethyl acetate extracts were dried over magnesium sulfate and evaporated to provide 0.109 g (94%) of 5-(ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylic acid as a white solid which was directly used in the next step.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialCombined ethyl acetate extracts were dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a33e4c114a6d44968af2067ac1f3ed7c
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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