Hydrochloric Acid → 2-(4-Methoxybenzyl)oxazole-4-carboxylic Acid

HRID 2217322Notes

Reaction equation

HRID 2217322 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[O:8][CH:9]=1)=[O:4].CO.[OH-].[Na+].Cl>O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][C:7]2[O:8][CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67234103HCID 67234103, compound

Product 1

HCID 667238322-(4-Methoxybenzyl)oxazole-4-carboxylic AcidYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-Methoxy-benzyl)-oxazole-4-carboxylic acid methyl ester (40 mg, 0.16 mmol), methanol (2 mL) and 1N NaOH (1 mL) was heated at 60° C. for 2 hours and allowed to stand at 25° C. for 30 minutes. After dilution with water, the mixture was adjusted to pH 2 with 2N HCl and extracted with ether. The organic layers were combined, dried with MgSO4 and evaporated to dryness to yield 25 mg (66%) of 2-(4-Methoxy-benzyl)-oxazole-4-carboxylic acid as a white solid. ESI-MS m/z calc. 233.2, found 234.2 (M+1)+. Retention time of 2.27 minutes.

Workup

  1. extractionextracted with ether
  2. dry with materialdried with MgSO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-a559c6627f494bed901695be9e4bcb08
Source dataset
uspto-grants-2008_08
Patent number
US07407976B2

Reaction notes

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