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

HRID 875334Notes

Reaction equation

HRID 875334 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1.Cl.C(OCC)(=O)C>C1(C)C=CC=CC=1.C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:24][CH:25]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86709825Methyl 4-[2-(4-fluorophenyl)ethyl]benzoate

Product 1

HCID 86709824{4-[2-(4-Fluorophenyl)ethyl]phenyl}methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under reflux, 45 ml of a 3.5 M solution of lithium aluminium hydride in toluene were slowly added dropwise to a solution of 35.4 g (136.98 mmol) of methyl 4-[2-(4-fluorophenyl)ethyl]benzoate in 500 ml of dry THF. After the addition had ended, the reaction mixture was stirred under reflux for one hour. The reaction mixture was then cooled to 0° C., and 500 ml of ice-cooled 1 M hydrochloric acid were added slowly and carefully. 750 ml of ethyl acetate were then added, the aqueous phase was removed 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 31.5 g (136.7 mmol, 99.9% of theory) of the title compound.

Workup

  1. temperatureUnder reflux
  2. additionAfter the addition
  3. temperatureunder reflux for one hour
  4. additionwere added slowly
  5. customthe aqueous phase was removed
  6. washthe organic phase was washed successively in each case once with 1 M hydrochloric acid and saturated sodium chloride solution
  7. dry with materialThe organic phase was then dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6a64747862024278871e9bc33584cf52
Source dataset
uspto-grants-2015_03
Patent number
US08981104B2

Reaction notes

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