Acetic Acid → [5-Nitro-2-(phenylsulfanyl)phenyl]acetic acid

HRID 435679Notes

Reaction equation

HRID 435679 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](CC#N)[C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].O.S(=O)(=O)(O)O.[C:26]([OH:29])(=[O:28])[CH3:27]>>[N+:1]([C:4]1[CH:9]=[C:8]([CH2:27][C:26]([OH:29])=[O:28])[C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 21481140HCID 21481140, compound

Product 1

HCID 12362916[5-Nitro-2-(phenylsulfanyl)phenyl]acetic acid

Procedure

210.3 g of 3-nitro-6-(phenylthio)-phenylacetonitrile, 210 ml of water, 210 ml of concentrated sulphuric acid and 210 ml of acetic acid are heated to reflux for 20 hours. The mixture is cooled and extracted with ether. The organic phase is washed successively with water and aqueous sodium carbonate solution. The aqueous phase is made acid with hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, evaporated under reduced pressure and the residue recrystallised from benzene. There is obtained 3-nitro-6-(phenylthio)-phenylacetic acid of melting point 138°-140° C.

Workup

  1. temperatureto reflux for 20 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with ether
  4. washThe organic phase is washed successively with water and aqueous sodium carbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customthe residue recrystallised from benzene

Sources & evidence

ORD record
ord-da3d81c198c74975b0699a20d0c3530b
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

Loading…