Ethanol → alpha-(Aminomethyl)-4-methoxybenzyl alcohol

HRID 1375142

Reaction equation

HRID 1375142 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](C=O)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:17]O.C(O)(=O)/C=C/C(O)=O.[CH2:27]([OH:29])[CH3:28]>>[NH2:17][CH2:28][CH:27]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:29]

Participants

6

Reactant 5

HCID 702EthanolHCID 787HydroxylamineHCID 312444-MethoxybenzaldehydeHCID 444972Fumaric AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 3016949alpha-(Aminomethyl)-4-methoxybenzyl alcohol

Procedure

2-Amino-1-(4-methoxyphenyl)ethanol was prepared according to the procedure of Evans et al., J. Org. Chem., 39, 914 (1974) by cyanosilylation of 4-methoxybenzaldehyde followed by lithium aluminum hydride reduction. The crude aminoalcohol (36.9 g) was dissolved in 150 mL of hot ethanol on a steam bath. To this mixture was slowly added 12.83 g of fumaric acid. The precipitated salt was filtered and washed with additional ethanol. Recrystallization from methanol provided greater than 99% pure 2:1 amine:fumarate salt.

Workup

  1. filtrationThe precipitated salt was filtered
  2. washwashed with additional ethanol
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-d5b66ae479b541ba8a29b81f52689dbd
Source dataset
uspto-grants-2007_01
Patent number
US07166696B2

Linked notes

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