3-Benzyloxy-4-methoxybenzaldehyde → HCID 23258950, compound

HRID 2052553Notes

Reaction equation

HRID 2052553 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:23]#[N:24])(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>[I-].[Zn+2].[I-].O1CCCC1>[NH2:24][CH2:23][CH:12]([C:11]1[CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[OH:13]

Participants

6

Reactant 3

HCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydride

Product 1

HCID 23258950HCID 23258950, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

50 mmol of 3-benzyloxy-4-methoxybenzaldehyde and 55 mmol of trimethylsilyl cyanide are heated together with 0.567 mmol of anhydrous zinc iodide for 4 hours under nitrogen and exclusion of moisture to 90°. The mixture is then taken up in 15 ml. of absolute tetrahydrofuran, and this solution is added dropwise to a suspension of 60 mmol of lithium aluminum hydride in 35 ml. of tetrahydrofuran. After heating the mixture for one hour to 60°, it is worked up as described in Example 1. Recrystallization from ethyl acetate produces 2-amino-1-(3-benzyloxy-4-methoxyphenyl)-ethanol, m.p. 100°-102°, in a 30% yield.

Workup

  1. custommoisture to 90°
  2. temperatureAfter heating the mixture for one hour to 60°, it
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-c57001132b10407fb6846f1ba4a38761
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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