Hydrochloric Acid → (2-Chloro-4-methylphenyl)methanol

HRID 2167885Notes

Reaction equation

HRID 2167885 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1.Cl.CCOCC>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2723981Borane;tetrahydrofuranHCID 27357552-Chloro-4-methylbenzoic acid

Product 1

HCID 15544016(2-Chloro-4-methylphenyl)methanolYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

as follows: To a solution of 2-chloro-4-methylbenzoic acid (2.18 g; 12.8 mmol) in THF (22 mL) was added dropwise a solution of BH3.THF in THF (25.6 ml; 1.00 mol/l; 25.6 mmol), at 0° C. Upon complete addition the resulting mixture was heated under reflux, for 3 hours. Subsequently, the mixture was cooled to 0° C., 1M aqueous HCl (30 mL) was added dropwise, and the mixture was stirred for 10 min. Et2O (100 mL) was added and the layers were separated. The organic layer was washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford (2-chloro-4-methyl-phenyl)-methanol (1.80 g), which was used as such.

Workup

  1. customat 0° C
  2. additionUpon complete addition the resulting mixture
  3. temperaturewas heated
  4. temperatureunder reflux, for 3 hours
  5. customthe layers were separated
  6. washThe organic layer was washed with 1M aqueous HCl (2×), 5% aqueous NaHCO3 (2×), and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50db0fbaaa8e4b968395e9a42dc1411a
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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