Methanol → 3-Chloro-4-methylbenzyl alcohol

HRID 514432Notes

Reaction equation

HRID 514432 reaction equation
[Cl:1][C:2]1[CH:10]=CC(C(O)=O)=[C:4](C)[CH:3]=1.B.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1.CO>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:13]([CH2:17][OH:16])[CH:14]=[CH:15][C:3]=1[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 3482694-Chloro-2-methylbenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 1234863-Chloro-4-methylbenzyl alcoholYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-2-methylbenzoic acid (800 mg, 4.69 mmol) in THF (8 mL) that was cooled at 0° C., BH3THF (14 mL, 1M in THF) was added into the solution drop wise. The mixture was then stirred at r.t. overnight. Add methanol to the system at 0° C. slowly until no gas released. Remove the solvent and the residue was extracted with ethylacetate, concentrated the organic phase to give 894 mg of the title compound (85%). 1H NMR (400 MHz, CDCl3): δ 2.36 (3H, s), 4.63 (2H, s), 7.13-7.22 (2H, m), 7.35 (1H, s).

Workup

  1. customat 0° C.
  2. customRemove the solvent
  3. extractionthe residue was extracted with ethylacetate
  4. concentrationconcentrated the organic phase

Sources & evidence

ORD record
ord-38a7507c32b9419eaacca85077daa273
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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