Sulfuric Acid → HCID 19857181, compound

HRID 2073486Notes

Reaction equation

HRID 2073486 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.OS(O)(=O)=O>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 19857177HCID 19857177, compound

Product 1

HCID 19857181HCID 19857181, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

165 g (0.53 mol) of 4,5-bis(4-fluorophenyl)-4-hydroxypentyl chloride were hydrogenated in 1,650 ml of glacial acetic acid, with the addition of 16.5 g of palladium-on-charcoal (10%) and 80 ml of concentrated H2SO4, at room temperature for 5 hours. The catalyst was filtered off with suction, the filtrate was concentrated to about one quarter of the volume, methylene chloride and water were added, the pH was brought to 6 with concentrated NaOH and the organic phase was separated off, washed with NaHCO3 solution and water, dried and concentrated.

Workup

  1. filtrationThe catalyst was filtered off with suction
  2. concentrationthe filtrate was concentrated to about one quarter of the volume, methylene chloride and water
  3. additionwere added
  4. customthe organic phase was separated off
  5. washwashed with NaHCO3 solution and water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae0e1cc8f71848d9bb5b19e43cc39ce5
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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