Boron trifluoride etherate → p-Cyanobenzyl alcohol

HRID 2242230Notes

Reaction equation

HRID 2242230 reaction equation
B(F)(F)F.CCOCC.[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)#[N:11]>C1COCC1>[OH:17][CH2:16][C:15]1[CH:19]=[CH:20][C:12]([C:10]#[N:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 120874-Cyanobenzoic acid

Product 1

HCID 160549p-Cyanobenzyl alcoholYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride diethyl etherate (0.85 mL, 6.8 mmol) was added to a solution of 4-cyanobenzoic acid (1.0 g, 6.8 mmol) and THF (10 mL). At room temperature, borane-tetrahydrofuran complex (1.0 M, 13.6 mL) was added to the reaction mixture drop-wise with no observed exotherm. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The resulting residue was taken up in ethyl acetate (50 mL), washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (0.900 g, 95% yield) as a solid.

Workup

  1. additionAt room temperature, borane-tetrahydrofuran complex (1.0 M, 13.6 mL) was added to the reaction mixture drop-wise with no observed exotherm
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56543ccd116644608e01777905e34a2e
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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