Hydrochloric Acid → 4-[5-[4-(6-Methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid

HRID 1816690Notes

Reaction equation

HRID 1816690 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:17][CH:16]=3)[O:12][N:11]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:29][O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[O:12][N:11]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=3)[CH:14]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 543928284-[5-[4-(6-Methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid methyl ester

Product 1

HCID 224929194-[5-[4-(6-Methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acidYield 99.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-[4-(6-methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid methyl ester (1.0 g) in a mixture of ethanol (10 ml) and tetrahydrofuran (20 ml) was added 10% sodium hydroxide aqueous solution (4.4 ml) and refluxed for 1 hour. The reaction mixture was adjusted to pH 1-2 with 1N-hydrochloric acid, and the resulting precipitate was collected by filtration to give 4-[5-[4-(6-methoxyhexyloxy)phenyl]isoxazol-3-yl]benzoic acid (964.2 mg).

Workup

  1. temperaturerefluxed for 1 hour
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-32e6fd1b3fce4ac89cd74980912710ab
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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