Hydrochloric Acid → HCID 59457455, compound

HRID 1710754Notes

Reaction equation

HRID 1710754 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:18]([O:20]C)=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.CO.[OH-].[Na+].Cl>O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:18]([OH:20])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59457502HCID 59457502, compound

Product 1

HCID 59457455HCID 59457455, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazole-5-carboxylate ax60 (4.0 g, 12.9 mmol, 1 eq) in a 1:1 mixture of methanol and water (100 ml) is treated with a 1 M solution of sodium hydroxide (14 ml, 14 mmol, 1.1 eq). The mixture is stirred at 60° C. during 2 h, then the mixture is concentrated. The residue is taken up in water (20 ml) and a 1 M hydrochloric acid solution (14 ml, 14 mmol, 1.1 eq) is added. The resulting suspension is filtered and the filtrate is concentrated to give 3.4 g of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazole-5-carboxylic acid i43.

Workup

  1. concentrationthe mixture is concentrated
  2. filtrationThe resulting suspension is filtered
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-140aff178e0747c5b72904717254b8fc
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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