Methanol → 2-(3-Methoxy-4-methylphenyl)ethanol

HRID 1511887Notes

Reaction equation

HRID 1511887 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11](O)=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9].CO.CCOC(C)=O.CCCCCCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 91183902-(3-Methoxy-4-methylphenyl)acetic acidHCID 21899848Ethylacetate heptane

Product 1

HCID 575395812-(3-Methoxy-4-methylphenyl)ethanolYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-methoxy-4-methylphenyl)acetic acid (1 g, 5.55 mmol) was dissolved in Tetrahydrofuran (27.7 ml). A solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly under nitrogen. The reaction was stirred for about 18 h. Methanol was slowly to quench the reaction. The mixture was rotovapped. More methanol was added. The mixture was rotovapped. This was repeat two more times. The solution was passed through a short pad of silica gel eluting with 1:1 EtOAc/heptane and then rotovapped to give 2-(3-methoxy-4-methylphenyl)ethanol (0.800 g, 4.81 mmol, 87% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.07 (dd, 1H), 6.73 (dd, 1H), 6.69 (s, 1H), 3.86 (t, 2H), 3.30 (s, 3H), 2.84 (t, 2H), 2.14 (s, 3H), 1.41 (s, 1H)

Workup

  1. additionA solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly under nitrogen
  2. customto quench
  3. customthe reaction

Sources & evidence

ORD record
ord-542d105b2dc24f6fb9e266e2316ea63c
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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