Tetrahydrofuran → Benzoic Acid

HRID 395599Notes

Reaction equation

HRID 395599 reaction equation
ClC1C=CC(C2N=C(N3C=CN=C3C)OC=2CCCCO[C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=CC=1.O1CCCC1.[OH-].[Na+]>C(O)C>[C:22]([OH:24])(=[O:23])[C:21]1[CH:26]=[CH:27][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12085644HCID 12085644, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
62.5 °C

Procedure

To a mixture of methyl 4-[4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butoxy]benzoate (1.86 g), tetrahydrofuran (20 ml) and ethanol (10 ml) was added 15 ml of a 1 N aqueous solution of sodium hydroxide, and the resulting mixture was stirred at 60-65° C. for 3 hours. The reaction mixture was concentrated and then diluted with a 10% aqueous solution of citric acid, and the resulting precipitate was filtered, washed with water and air-dried to give crystals of 4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butoxy]benzoic acid. Recrystallization from tetrahydrofuran-isopropyl ether gave colorless prisms (1.15 g, 51%). Melting point 214-216° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with a 10% aqueous solution of citric acid
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-50285dbddbaf4e0e9ad61c5cbc817abd
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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