Ammonium Chloride → 1-(2-Methoxy-4-methyl-phenyl)-propan-1-ol

HRID 1671358Notes

Reaction equation

HRID 1671358 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[CH3:12][CH2:13][Mg+].[Br-].[Cl-].[NH4+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:4]=1[CH:5]([OH:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 64237932-Methoxy-4-methylbenzaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 672125481-(2-Methoxy-4-methyl-phenyl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirring solution of 2-methoxy-4-methylbenzaldehyde (1 g, 6.66 mmol) in diethyl ether (35 ml) at 0° C. is added EtMgBr (2.220 ml, 6.66 mmol). The mixture is stirred for 2 hours and then added to sat ammonium chloride solution. The mixture is extracted with ethyl acetate and the combined organic portions are washed with NaHCO3, water and brine dried (MgSO4) and reducing under vacuum to yield the title product as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.18 (d, 1H), 6.78 (d, 1H), 6.72 (s, 1H), 4.77 (t, 1H), 3.85 (s, 3H), 2.37 (s, 3H), 1.83 (m, 2H), 0.96 (t, 3H).

Workup

  1. additionadded
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe combined organic portions are washed with NaHCO3, water and brine
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0978c5cdbfdb4018beb525bac7e36a37
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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