Methanol → HCID 15725733, compound

HRID 982086Notes

Reaction equation

HRID 982086 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C[N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:13]1.O.[OH-].[Li+].CO.O>C(OCC)C>[C:23]1([C:14]2[C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][N:12]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:10])=[O:9])[N:13]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67794290HCID 67794290, compound

Product 1

HCID 15725733HCID 15725733, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3,4-diphenyl-lH-pyrazole 1-octanoate (3.40 g, 9 mmol), lithium hydroxide hydrate (1.13 g, 27 mmol), methanol (60 mL), and water (10 mL) was heated at reflux on a steam bath. After 15 minutes, the solution was concentrated in vacuo, diluted with water and 2 N HCl solution until pH =1. The mixture was extracted with methylene chloride, the combined extracts dried, and the solvent evaporated to leave an oil. Dissolution in diethyl ether followed by the addition of hexanes provided 3,4-diphenyl-lH-pyrazole-1-octanoic acid (2.80 g, 86%); m.p. =108°-110° C. MS(CI): m/e =363 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux on a steam bath
  3. concentrationthe solution was concentrated in vacuo
  4. additiondiluted with water and 2 N HCl solution
  5. extractionThe mixture was extracted with methylene chloride
  6. customthe combined extracts dried
  7. customthe solvent evaporated
  8. customto leave an oil

Sources & evidence

ORD record
ord-07ac510f7a55416eb634456fecc05a37
Source dataset
uspto-grants-1991_02
Patent number
US04994482

Reaction notes

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