1'-Hydroxymethyleugenol

Base Information

• Chemical Name: 1'-Hydroxymethyleugenol
• CAS No.: 31706-95-3
• Molecular Formula: C11H14 O3
• Molecular Weight: 194.23
• European Community (EC) Number: 848-041-0
• UNII: DA6575YC8S
• DSSTox Substance ID: DTXSID20953660
• Nikkaji Number: J529.684F
• Wikidata: Q27276301
• Mol file: 31706-95-3.mol

Synonyms:1'-(hydroxymethyl)eugenol;1'-hydroxymethyleugenol

Chemical Property of 1'-Hydroxymethyleugenol

Chemical Property:

• Vapor Pressure: 0.000342mmHg at 25°C
• Refractive Index: 1.4600 (estimate)
• Boiling Point: 306.2°Cat760mmHg
• Flash Point: 139°C
• PSA: 38.69000
• Density: 1.078g/cm³
• LogP: 1.92320
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

ALPHA-ETHENYL-3,4-DIMETHOXY-BENZENEMETHANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(C=C)O)OC

Technology Process of 1'-Hydroxymethyleugenol

There total 5 articles about 1'-Hydroxymethyleugenol 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: 100.0%

vinyl magnesium bromide (1826-67-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 1'-Hydroxymethyleugenol (31706-95-3)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c6ob01915c

Reference yield: 88.0%

vinyl magnesium bromide (1826-67-1) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → 1'-Hydroxymethyleugenol (31706-95-3)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol4037055

Reference yield:

1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one (104397-78-6) → 1'-Hydroxymethyleugenol (31706-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; triphenylphosphine; tetra-(n-butyl)ammonium iodide / dichloromethane / 2 h / 20 - 25 °C

1.2: 1 h / 20 - 25 °C

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; tetra-(n-butyl)ammonium iodide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane;

DOI:10.1002/chem.201604788

upstream raw materials:

4-Bromoveratrole

acrolein

vinyl magnesium bromide

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

2-(3',4'-dimethoxycinnamyl)-2-methylcyclopentane-1,3-dione

1-(3,4-dimethoxyphenyl)prop-2-en-1-one

(S)-1-(3',4'-dimethoxyphenyl)prop-2-en-1-ol

C₁₃H₁₆O₄

Refernces

• 1、 Antoniotti, Sylvain,Blerot, Bernard,Chietera, Giorgiana,Lecourt, Mathilde. "Laccase-catalyzed oxidation of allylbenzene derivatives: Towards a green equivalent of ozonolysis". supporting information. . Retrieved 2021/10/19.
• 2、 Chinnabattigalla, Sreenivasulu,Choudhury, Aditya,Gedu, Satyanarayana. "[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols". supporting information. p. 8259 - 8263. Retrieved 2021/10/12.