Hydrochloric Acid → Seratrodast

HRID 2254351Notes

Reaction equation

HRID 2254351 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].Cl.[OH2:27]>C(#N)C.N.N(S([O-])(=O)=O)(S([O-])(=O)=O)[O].[K+].[K+]>[CH3:10][C:4]1[C:5](=[O:27])[C:6]([CH3:9])=[C:7]([CH3:8])[C:2](=[O:1])[C:3]=1[CH:11]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 145139667-(2-Hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid

Product 1

HCID 2449SeratrodastYield 94.1%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 6342AcetonitrileSolventHCID 3032624Potassium nitrosodisulfonateSolvent

Procedure

7-(2-hydroxy-3,4,6-trimethylphenyl)-7-phenylheptanoic acid (5.0 g) was dissolved in a mixed solution of acetonitrile (25 ml), water (10 ml) and 25% aqueous ammonia (1 ml), to which 3% aqueous solution (280 ml) of potassium nitrosodisulfonate (Fremy's salt) was added. The mixture was stirred at a temperature of 2° to 4° C. for 2 hours. The reaction mixture was acidified with hydrochloric acid, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water twice. Ethyl acetate was distilled off under reduced pressure, and the residue was recrystalized from a mixed solution of acetonitrile and water (6:4) to give 7-(3,5,6-trimethyl-1,4-benzoquinone-2-yl)-7-phenylheptanoic acid (4.90 g, 94.1%) as yellow crystals.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water twice
  4. distillationEthyl acetate was distilled off under reduced pressure
  5. customthe residue was recrystalized from a mixed solution of acetonitrile and water (6:4)

Sources & evidence

ORD record
ord-f36bdf47dde04005bcac95d3661a57ff
Source dataset
uspto-grants-1993_08
Patent number
US05235091

Reaction notes

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