Sulfuric Acid → 3,3-Bis(4-fluorophenyl)propanol

HRID 2073480Notes

Reaction equation

HRID 2073480 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].OS(O)(=O)=O>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9855836Potassium sodium tartarateHCID 102208743,3-bis(4-fluorophenyl)propanoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 197832883,3-Bis(4-fluorophenyl)propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

57.9 g (0.221 mol) of 3,3-bis(4-fluorophenyl)propionic acid were dissolved in 200 ml of absolute ether and the solution was added dropwise to a suspension of 10.9 g (0.287 mol) of LiAlH4 in 150 ml of absolute ether. When the dropwise addition had ended, the mixture was subsequently stirred for a further 30 minutes and, for hydrolysis, 175 ml of saturated sodium potassium tartrate solution and 400 ml of 10% strength H2SO4 were added dropwise in succession. After filtration, the phases were separated and the ethereal phase was washed with NaHCO3 solution and NaCl solution, dried and concentrated.

Workup

  1. additionWhen the dropwise addition
  2. additionwere added dropwise in succession
  3. filtrationAfter filtration
  4. customthe phases were separated
  5. washthe ethereal phase was washed with NaHCO3 solution and NaCl solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-17ad3e6a6e784ff18582e0fbab59a81a
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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