Sodium Hydroxide → HCID 59457489, compound

HRID 1710751Notes

Reaction equation

HRID 1710751 reaction equation
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=2)=[CH:10][CH:9]=1>C(O)C>[Cl:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59457496HCID 59457496, compound

Product 1

HCID 59457489HCID 59457489, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 N aqueous solution of sodium hydroxide (10 ml, 20.3 mmol, 3 eq) is added dropwise to a solution of ethyl 2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole-4-carboxylate i33 (2.1 g, 6.8 mmol, 1 eq) in ethanol (60 ml). The mixture is refluxed for 2 h 30 and the solvent is evaporated. The residue is taken up in water and acidified to pH 2 with a 2 N hydrochloric acid solution. The solid that precipitates is filtered off and washed with water to give 1.5 g of 2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole-4-carboxylic acid i34.

Workup

  1. temperatureThe mixture is refluxed for 2 h 30
  2. customthe solvent is evaporated
  3. customThe solid that precipitates
  4. filtrationis filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-ede45e86dc924ab392bd75706f44f10d
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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