Acetic Acid → 5-(Methoxymethyl)-1,2-oxazole-4-carboxylic acid

HRID 1094802Notes

Reaction equation

HRID 1094802 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[CH:6][C:5]=1[C:9]([O:11]C)=[O:10].Cl.C(O)(=O)C.O>CC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[O:8][N:7]=[CH:6][C:5]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 14787242HCID 14787242, compound

Product 1

HCID 147872515-(Methoxymethyl)-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 5-(methoxymethyl)isoxazole-4-carboxylate (Preparation 42, 1.8 g, 11 mmol) was stirred in a 1:1:1 mixture of concentrated hydrochloric acid (2 ml), acetic acid (2 ml) and water (2 ml) at reflux for 6 hours. Acetone (6 ml) was added and the mixture concentrated in vacuo. The solid residue was triturated with ethyl acetate and the filtrate concentrated in vacuo to afford the title compound as an off white solid (1.4 g, 85% yield).

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationthe mixture concentrated in vacuo
  3. customThe solid residue was triturated with ethyl acetate
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ba0c447e30bf4982a99d930cff454302
Source dataset
uspto-grants-2012_03
Patent number
US08134007B2

Reaction notes

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