Borane → 2-(2,4-Dimethylphenyl)ethanol

HRID 2379768Notes

Reaction equation

HRID 2379768 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH2:4]O.B.C1C[O:15][CH2:14]C1>>[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH2:4][CH2:14][OH:15]

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 278092,4-Dimethylbenzyl alcohol

Product 1

HCID 2474782-(2,4-Dimethylphenyl)ethanol

Procedure

A solution of carboxylic acid 9 (3.40 g; 17.87 mmol) in THF (100 ml) was cooled to 0° C. and treated with 35 ml of a 1.0M solution of borane in THF. After stirring this mixture overnight it was quenched with 1N HCl and the product was extracted into ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of solvent. The crude product was filtered through a plug of silica gel eluting with 20% ethyl acetate in hexane to obtain 2.75 g (quantitative yield) of the product as a clear light oil. 1H NMR (CDCl3): δ2.25, 2.28 (s, 3H each); 2.88 (t, 2H); 3.78 (t, 2H); 6.97-7.07 (m, 3H). IR (neat): 3340, 2947, 1504, 1448, 1265, 1044 cm-1.

Workup

  1. customwas quenched with 1N HCl
  2. extractionthe product was extracted into ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationThe crude product was filtered through a plug of silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7816546a6ee84e31a3ee5df968feb920
Source dataset
uspto-grants-1994_11
Patent number
US05364876

Reaction notes

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