Hydrochloric Acid → (2,6-Diethylphenyl)methanol

HRID 920571Notes

Reaction equation

HRID 920571 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:4]=1[CH:5]=[O:6])[CH3:2].B.C1COCC1.Cl.CCOCC>C1COCC1>[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:4]=1[CH2:5][OH:6])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2723981Borane;tetrahydrofuranHCID 131847782,6-Diethylbenzaldehyde

Product 1

HCID 13383922(2,6-Diethylphenyl)methanolYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-diethyl-benzaldehyde (0.68 g; 4.19 mmol) in THF (15 mL) was added dropwise a solution of BH3.THF in THF (8.38 ml; 1.00 mol/l; 8.38 mmol), at 0° C. After complete addition the mixture was heated under reflux for 3 hours. Subsequently, the resulting mixture was cooled to 0° C. and 1M aqueous HCl (10 ml) was added dropwise. The mixture was allowed to warm to room temperature (˜10 min.), and treated with Et2O. The layers were separated, the organic layer washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford (2,6-diethyl-phenyl)-methanol (0.67 g), which was used as such.

Workup

  1. customat 0° C
  2. additionAfter complete addition the mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 3 hours
  5. temperatureto warm to room temperature (˜10 min.)
  6. customThe layers were separated
  7. washthe organic layer washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d819f4c4418f4a11a9c517ba52f011b3
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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