2,2,2-Trifluoroethanol → HCID 58542848, compound

HRID 1918206Notes

Reaction equation

HRID 1918206 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([F:11])=[C:4](F)[C:3]=1[F:13].[F:14][C:15]([F:19])([F:18])[CH2:16][OH:17].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[F:10][C:6]1[C:5]([F:11])=[C:4]([O:17][CH2:16][C:15]([F:19])([F:18])[F:14])[C:3]([F:13])=[C:2]([F:1])[C:7]=1[CH:8]=[O:9]

Participants

7

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 14798Sodium HydroxideHCID 69558Pentafluorobenzaldehyde

Product 1

HCID 58542848HCID 58542848, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Pentafluorobenzaldehyde (Oakwood Products, cat. #002835, 19.6 g, 0.1 mol) and tetrabutylammonium hydrogensulfate, Bu4NHSO4 (50 mg, 0.0015 mol) are dissolved in 500 ml CH2Cl2. 2,2,2-Trifluoroethanol (10.0 g, 0.01 mol) is added and the mixture is stirred and cooled in an ice-bath. Sodium hydroxide pellets (4.0 g, 0.01 mol) are dissolved in 100 ml of water and slowly added to the mixture with a dropping funnel. The temperature of the mixture is monitored. The rate of addition controlled to keep the temperature below 5° C. After addition is complete the mixture is stirred for an additional 2 h at 5° C. and then transferred to a separatory funnel. The organic layer is separated and dried with Na2SO4. The solvent is evaporated using a rotovap and the residual oil is fractionally distilled with a short path apparatus. The fraction with a boiling range of 105-108° C. contains the desired compound.

Workup

  1. temperaturecooled in an ice-bath
  2. additionslowly added to the mixture with a dropping funnel
  3. additionThe rate of addition
  4. customthe temperature below 5° C
  5. additionAfter addition
  6. stirringis stirred for an additional 2 h at 5° C.
  7. customtransferred to a separatory funnel
  8. customThe organic layer is separated
  9. dry with materialdried with Na2SO4
  10. customThe solvent is evaporated
  11. distillationthe residual oil is fractionally distilled with a short path apparatus

Sources & evidence

ORD record
ord-3d6f3125f7134bf6a50531b84729d13f
Source dataset
uspto-grants-2013_12
Patent number
US08618302B2

Reaction notes

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