Hydrochloric Acid → (+)-2-(Pentafluorophenyl)-1-propanol

HRID 2248998Notes

Reaction equation

HRID 2248998 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[CH:4]1[O:6][CH2:5]1.[CH3:15][Al](C)C.Cl>ClCCl.CCCCCC>[F:1][C:2]1[C:3]([CH:4]([CH3:15])[CH2:5][OH:6])=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[C:10]=1[F:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27759812-(2,3,4,5,6-Pentafluorophenyl)oxiraneHCID 16682925Trimethylaluminum

Product 1

HCID 14651851(+)-2-(Pentafluorophenyl)-1-propanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 10.5 g of (+)-2,3,4,5,6-pentafluorostyrene oxide (over 95%ee) in 50 ml of dichloromethane was added dropwise to 100 ml of a 1.0M solution of trimethylaluminum in hexane, and was reacted for 40 hours at room temperature. This reaction mixture was poured into 100 ml of 1N hydrochloric acid. After the aqueous layer was extracted with ether, the total organic solution was dried over magnesium sulfate. The solvent was distilled out under reduced pressure, and the subsequent distillation under reduced pressure gave 10.6 g of (+)-2-(pentafluorophenyl)-1-propanol having the aforementioned physical properties.

Workup

  1. customwas reacted for 40 hours at room temperature
  2. extractionAfter the aqueous layer was extracted with ether
  3. dry with materialthe total organic solution was dried over magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure
  5. distillationthe subsequent distillation under reduced pressure

Sources & evidence

ORD record
ord-91e3bfd29f7d49378b590d1f2e613519
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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