Hydrochloric Acid → HCID 20568371, compound

HRID 905160Notes

Reaction equation

HRID 905160 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:11])[C:9]#N)[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-:18].[Na+].[OH2:20].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:11])[C:9]([OH:20])=[O:18])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:11][CH:8]([C:9]([OH:20])=[O:18])[C:6]1[CH:5]=[CH:4][C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 13020232HCID 13020232, compound

Product 1

HCID 20568371HCID 20568371, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.8 g (16.9 mmol) of the propionitrile (5) prepared according to the procedure of Example 11 (melting point 69°-72° C.), 3.5 g (87 mmol) of NaOH, 25 ml of H2O and 25 ml of CH3OH was allowed to reflux for 16 hours. The resulting clear, colorless solution was acidified with HCl and extracted with Et2O. The resulting Et2O solution was dried and concentrated to yield 4.0 g (98%) of the propionic acid (6) as a colorless solid having a melting point of 109°-113° C. According to the Merck Index, Ninth Edition, 1976, pure flurbiprofen melts at 113°-114° C.

Workup

  1. customprepared
  2. temperatureto reflux for 16 hours
  3. extractionextracted with Et2O
  4. dry with materialThe resulting Et2O solution was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9bc7b628b0cb487396bd11e9a455bbbd
Source dataset
uspto-grants-1983_12
Patent number
US04422979

Reaction notes

Loading…