Hydrochloric Acid → (4-{2-[4-(Trifluoromethyl)phenyl]ethyl}phenyl)methanol

HRID 875343Notes

Reaction equation

HRID 875343 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:28])([F:27])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.Cl.C(OCC)(=O)C>C1COCC1>[F:7][C:8]([F:27])([F:28])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:26]=[CH:25][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14857441Methyl 4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 86709834(4-{2-[4-(Trifluoromethyl)phenyl]ethyl}phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature and under argon, 12.3 ml of a 1 M solution of lithium aluminium hydride in THF were slowly added dropwise to a solution of 11.5 g (37.30 mmol) of methyl 4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzoate in 150 ml of dry THF. After the addition had ended, the reaction mixture was stirred at room temperature for another hour. The reaction mixture was then cooled to 0° C., and 150 ml of ice-cooled 1 M hydrochloric acid were added slowly and carefully. About 250 ml of ethyl acetate were then added, the aqueous phase was separated off and the organic phase was washed successively in each case once with 1 M hydrochloric acid and saturated sodium chloride solution. The organic phase was then dried over magnesium sulphate, filtered and concentrated to dryness. This gave 9.69 g (34.57 mmol, 93% of theory) of the title compound.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. additionwere added slowly
  4. customthe aqueous phase was separated off
  5. washthe organic phase was washed successively in each case once with 1 M hydrochloric acid and saturated sodium chloride solution
  6. dry with materialThe organic phase was then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b8be0cc5d482402fa45ef88e47a1f0ce
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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