Methanol → HCID 15725733, compound

HRID 1460716Notes

Reaction equation

HRID 1460716 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-1H-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 2N 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-1H-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 2N HCl solution until pH=1
  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-1994b660432a47fea1cb6aead7982ce1
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

Loading…