Thioglycolic Acid → HCID 20348735, compound

HRID 1701158Notes

Reaction equation

HRID 1701158 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[CH:10][CH:9]=1.FC1C=CC=CC=1C1C=CC(CC(CC2C=CC(C3C=CC=CC=3F)=CC=2)=O)=CC=1.[BH4-].[Na+].[SH:49][CH2:50][C:51]([OH:53])=[O:52].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([S:49][CH2:50][C:51]([OH:53])=[O:52])[CH3:15])=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 1133Thioglycolic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 13519938HCID 13519938, compoundHCID 544884792'-Fluoro-4-biphenylyl-methyl-ketone

Product 1

HCID 20348735HCID 20348735, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

50 gm (0.23 mol) of 1-(2'-fluoro-4-biphenylyl)-1-hydroxy-ethane, m.p. 88° C., (prepared from 2'-fluoro-4-biphenylyl-methyl-ketone by reduction with sodium borohydride in methanol) were dissolved in 500 ml of benzene, 32.2 gm (0.276 mol) of 80% mercapto-acetic acid and 1 gm of p-toluenesulfonic acid were added, and the mixture was heated at its boiling point for 1 hour, using an apparatus equipped with a water trap. 20.5 ml of water were separated. The benzene solution was washed with water after cooling, dried and evaporated. The crystalline residue was recrystallized from benzene/cyclohexane (2:1), whereby 38.0 gm (61.5% of theory) of the title compound, m.p. 125°-127° C., were obtained.

Workup

  1. temperaturethe mixture was heated at its boiling point for 1 hour
  2. customequipped with a water trap
  3. custom20.5 ml of water were separated
  4. washThe benzene solution was washed with water
  5. temperatureafter cooling
  6. customdried
  7. customevaporated
  8. customThe crystalline residue was recrystallized from benzene/cyclohexane (2:1), whereby 38.0 gm (61.5% of theory) of the title compound, m.p. 125°-127° C.
  9. customwere obtained

Sources & evidence

ORD record
ord-f4501e07a2e4490f942fc150eeaaa7a7
Source dataset
uspto-grants-1980_03
Patent number
US04191776

Reaction notes

Loading…