Hydrochloric Acid → 4-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acid

HRID 1386597Notes

Reaction equation

HRID 1386597 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=3)[CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].O1CCCC1.[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=3)[CH:14]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21182302Ethyl 4-[5-(4-n-pentyloxyphenyl)-isoxazol-3-yl]benzoate

Product 1

HCID 99752244-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acidYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 4-[5-(4-n-pentyloxyphenyl)-isoxazol-3-yl]benzoate (6.33 g) in ethanol 60 ml) and tetrahydrofuran (90 ml) was added 2N sodium hydroxide aqueous solution (12.5 ml) at 80° C. The mixture was refluxed for 1 hour and poured into ice-water. The suspension was adjusted to pH 2.0 with 1N HCl. The precipitate was collected by filtration, washed with water and dried to give 4-[5-(4-n-pentyloxyphenyl)isoxazol-3-yl]benzoic acid (5.80 g).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-2290ea0578cc4f3facdc62d6f4dd2ef6
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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