Hydrochloric Acid → 7-(4-Phenyloxazol-2-yl)heptanoic acid

HRID 1039145Notes

Reaction equation

HRID 1039145 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1.Cl>O.CO>[C:17]1([C:15]2[N:16]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:23])=[O:4])[O:13][CH:14]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59167767HCID 59167767, compound

Product 1

HCID 684916247-(4-Phenyloxazol-2-yl)heptanoic acidYield 91.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Add solution of sodium hydroxide (1.60 g, 40.0 mmol) in water (30 mL) to a solution of 7-(4-phenyloxazol-2-yl)heptanoic acid methyl ester (5.75 g, 20.0 mmol) in methanol (40 mL) at room temperature and heat the mixture at 40° C. for 2 hours. Adjust the pH of the mixture to 2 with 1 N HCl and extract with ethyl acetate (600 mL). Wash the organic extract with water (3×150 mL), dry over sodium sulfate and remove the solvent under reduced pressure. Triturate the residue with hexanes/ethyl acetate and collect the solids by filtration to provide 7-(4-phenyloxazol-2-yl)heptanoic acid (5.01 g, 91%): APCI mass spectrum m/z 272 [C16H19NO3−H]−.

Workup

  1. extractionextract with ethyl acetate (600 mL)
  2. washWash the
  3. extractionorganic extract with water (3×150 mL)
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customTriturate the residue with hexanes/ethyl acetate
  7. customcollect the solids
  8. filtrationby filtration

Sources & evidence

ORD record
ord-1322a40509084c54a53dab00c5d229c8
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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