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

HRID 58541Notes

Reaction equation

HRID 58541 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-0abeed7643944a57a89e3ae03bfb6d87
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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