Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate → 1-[3-(2-Dioxolanyl)-propoxy]-pyrazole-4-carboxylic acid

HRID 232019Notes

Reaction equation

HRID 232019 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][O:9][N:10]1[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[N:11]1>[OH-].[Na+]>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][CH2:7][CH2:8][O:9][N:10]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[N:11]1

Participants

3

Reactant 1

HCID 13823206Methyl 1-[3-(2-dioxolanyl)-propoxy]-pyrazole-4-carboxylate

Product 1

HCID 138232071-[3-(2-Dioxolanyl)-propoxy]-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

151 g of the above product from (a) are stirred with 650 ml of 2N sodium hydroxide solution at 90° C. until a clear solution has formed. The solution is cooled and then washed with 200 ml of methylene chloride, the aqueous phase is acidified with concentrated hydrochloric acid and extracted several times with methylene chloride, and the extract is dried and evaporated down to give a colorless residue which crystallizes spontaneously. Yield: 129 g (88% of theory, based on methyl 1-hydroxypyrazole-4-carboxylate). M.p.: 85° C.

Workup

  1. customhas formed
  2. temperatureThe solution is cooled
  3. washwashed with 200 ml of methylene chloride
  4. extractionextracted several times with methylene chloride
  5. customthe extract is dried
  6. customevaporated down
  7. customto give a colorless residue which
  8. customcrystallizes spontaneously

Sources & evidence

ORD record
ord-aa7a8ecdaee24c5096f3066089c40040
Source dataset
uspto-grants-1989_07
Patent number
US04851410

Reaction notes

Loading…