Carbon Dioxide → HCID 178444273, compound

HRID 727758Notes

Reaction equation

HRID 727758 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl-].[Al+3].[Cl-].[Cl-].C(=O)=O.[F:31][C:32]([F:37])([F:36])[C:33](Cl)=[O:34].Cl>[C]=S>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:33](=[O:34])[C:32]([F:37])([F:36])[F:31])=[CH:22][CH:23]=3)=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 61106Trifluoroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178444253HCID 178444253, compound

Product 1

HCID 178444273HCID 178444273, compound

Reagents, catalysts & solvents 1

HCID 178503046HCID 178503046, compoundSolvent

Procedure

0.5 mol of 4-(trans-4-pentylcyclohexyl)biphenyl, 500 ml of carbon sulfide and 0.5 mol of aluminium chloride are introduced into a three-neck flask fitted with a dry-ice reflux condenser. After the mixture has been cooled to -30°, 0.5 mol of trifluoroacetyl chloride are condensed in. The mixture is then allowed to warm to 0° and stirred at this temperature for 6 hours then at room temperature for 14 hours. The reaction mixture is poured onto a mixture of ice and dilute hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted by shaking with dichloromethane (2×50 ml). The organic phases are combined, the solvents removed by distillation and the product is recrystallized twice from ethanol.

Workup

  1. temperaturereflux condenser
  2. temperatureAfter the mixture has been cooled to -30°
  3. customcondensed in
  4. temperatureto warm to 0°
  5. waitat room temperature for 14 hours
  6. customThe organic phase is separated off
  7. extractionthe aqueous phase is extracted
  8. stirringby shaking with dichloromethane (2×50 ml)
  9. customthe solvents removed by distillation
  10. customthe product is recrystallized twice from ethanol

Sources & evidence

ORD record
ord-fc0f90bcff1744139f0b48dc85ae1ad1
Source dataset
uspto-grants-1991_09
Patent number
US05045229

Reaction notes

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