Hydrochloric Acid → 1-(Trifluoromethyl)cyclopropanemethanol

HRID 715122Notes

Reaction equation

HRID 715122 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>CCOCC>[F:1][C:2]([F:10])([F:9])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 509906611-(Trifluoromethyl)cyclopropanemethanolYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Treat a 0° C. solution of 1-(trifluoromethyl)cyclopropanecarboxylic acid (9 g, 58.4 mmol) in ether (140 mL), under N2, portion-wise with LAH (2.9 g, 76 mmol), allow to warm to RT and stir overnight. Re-cool to 0° C., slowly add HCl, warm to RT and separate the layers. Extract the aqueous layer with ether (2×), wash the combined organics with brine, dry over Na2SO4 and concentrate under reduced pressure (water bath temp<30° C.) to afford the title compound (7 g, 86%). 1HNMR (400 MHz, DMSO-d6): δ 4.94 (t, J=6.0 Hz, 1H), 3.54 (d, J=6.0 Hz, 2H), 0.87-0.84 (m, 2H), 0.81-0.79 (m, 2H).

Workup

  1. customseparate the layers
  2. extractionExtract the aqueous layer with ether (2×)
  3. washwash the combined organics with brine
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate under reduced pressure (water bath temp<30° C.)

Sources & evidence

ORD record
ord-fd38a5d0a3ab4cbe97e7ae5c034256d9
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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