alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile

Base Information

• Chemical Name: alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile
• CAS No.: 67387-77-3
• Molecular Formula: C16H15NO3
• Molecular Weight: 269.3
• DSSTox Substance ID: DTXSID201200306
• Mol file: 67387-77-3.mol

Synonyms:SCHEMBL11435943;alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile;DTXSID201200306;67387-77-3

Chemical Property of alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 269.10519334
• Heavy Atom Count: 20
• Complexity: 332

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(C#N)O)OCC2=CC=CC=C2

Technology Process of alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile

There total 3 articles about alpha-Hydroxy-4-methoxy-3-(phenylmethoxy)benzeneacetonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (3-Benzyloxy-4-methoxy-phenyl)-hydroxy-acetonitrile (67387-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaHSO₃ / methanol; H₂O / 1) 55 deg C, 2) RT, 4 h

2: H₂O; methanol / 0.33 h / Ambient temperature

With sodium hydrogensulfite; In methanol; water;

DOI:10.1248/cpb.37.1744

Reference yield:

trimethylsilyl cyanide (7677-24-9) + 3-benzyloxy-4-methoxybenzaldehyde (6346-05-0) → (3-Benzyloxy-4-methoxy-phenyl)-hydroxy-acetonitrile (67387-77-3)

Guidance literature:

With hydrogenchloride; zinc(II) iodide;

DOI:10.1016/S0040-4039(00)61966-4

Reference yield:

potassium cyanide (151-50-8) + Sodium; (3-benzyloxy-4-methoxy-phenyl)-hydroxy-methanesulfonate → (3-Benzyloxy-4-methoxy-phenyl)-hydroxy-acetonitrile (67387-77-3)

Guidance literature:

In methanol; water; for 0.333333h; Ambient temperature;

DOI:10.1248/cpb.37.1744

upstream raw materials:

potassium cyanide

trimethylsilyl cyanide

3-benzyloxy-4-methoxybenzaldehyde

Downstream raw materials:

Acetic acid 2-[acetyl-(2-iodo-benzyl)-amino]-1-(5-benzyloxy-2-iodo-4-methoxy-phenyl)-ethyl ester

O-acetyl-β-(5-benzyloxy-2-iodo-4-methoxyphenyl)-N-(2-iodobenzyl)-N-methylethanolamine

Acetic acid 2-(benzyl-methyl-amino)-1-(5-benzyloxy-2-iodo-4-methoxy-phenyl)-ethyl ester

8-acetoxy-10-benzyloxy-11-methoxy-6-methyl-5,6,7,8-tetrahydrodibenzazocine

Refernces

• 1、 Kihara,Vangveravong,Ohnishi,Imakura,Kobayashi. "Syntheses of apogalanthamine analogues as α-adrenergic blocking agents. XIII. Syntheses of phenolic 8-hydroxy-5,6,7,8-tetrahydrodibenz[c,e]azocines". . p. 1744 - 1747. Retrieved 2007/10/02.