(E)-4-[4-(3-Hydroxypropyl)phenoxy]-2-methyl-2-buten-1-ol

Base Information

• Chemical Name: (E)-4-[4-(3-Hydroxypropyl)phenoxy]-2-methyl-2-buten-1-ol
• CAS No.: 51593-96-5
• Molecular Formula: C14H20O3
• Molecular Weight: 236.311
• Hs Code.: 2909499000
• Mol file: 51593-96-5.mol

Synonyms:

Chemical Property of (E)-4-[4-(3-Hydroxypropyl)phenoxy]-2-methyl-2-buten-1-ol

Chemical Property:

• PSA: 49.69000
• LogP: 1.92890

Purity/Quality:

98%Min ^*data from raw suppliers

Cuspidiol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-4-[4-(3-Hydroxypropyl)phenoxy]-2-methyl-2-buten-1-ol

There total 17 articles about (E)-4-[4-(3-Hydroxypropyl)phenoxy]-2-methyl-2-buten-1-ol 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: 95.0%

(E)-3--1-propanol (130487-29-5) → 4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol (51593-96-5)

Guidance literature:

With zinc; In water; acetic acid; for 24h; Ambient temperature;

DOI:10.1246/bcsj.63.1328

Reference yield:

4-benzyloxybenzyl alcohol (836-43-1) → 4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol (51593-96-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.840 g / thionyl chloride / benzene; pyridine / 1 h / Ambient temperature

2: 0.603 g / NaH / paraffin; dimethylformamide / 3 h / Ambient temperature

3: 0.370 g / KON / ethanol; H₂O / 3 h / Heating

4: 0.249 g / 150 - 160 °C / 15 - 20 Torr

5: 1.663 g / diethyl ether / 2 h / Ambient temperature

6: 1.305 g / LiAlH₄ / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

7: 0.149 g / H₂ / 10percent Pd-charcoal / ethanol / Ambient temperature

8: 1.) N-bromosuccinimide, 2.) K₂CO₃ / 1.) CCl₄, reflux, 3 h, 2.) acetone, reflux, 8.5 h

9: 0.077 g / LiAlH₄ / tetrahydrofuran; diethyl ether / 1.) room temperature, 1h, 2.) reflux, 2 h

With N-Bromosuccinimide; lithium aluminium tetrahydride; thionyl chloride; KON; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; ethanol; water; N,N-dimethyl-formamide; paraffin; benzene;

Reference yield:

4-benzyloxybenzyl chloride (836-42-0) → 4-[4-(3-hydroxy-propyl)-phenoxy]-2-methyl-but-2-en-1-ol (51593-96-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 0.603 g / NaH / paraffin; dimethylformamide / 3 h / Ambient temperature

2: 0.370 g / KON / ethanol; H₂O / 3 h / Heating

3: 0.249 g / 150 - 160 °C / 15 - 20 Torr

4: 1.663 g / diethyl ether / 2 h / Ambient temperature

5: 1.305 g / LiAlH₄ / diethyl ether; tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

6: 0.149 g / H₂ / 10percent Pd-charcoal / ethanol / Ambient temperature

7: 1.) N-bromosuccinimide, 2.) K₂CO₃ / 1.) CCl₄, reflux, 3 h, 2.) acetone, reflux, 8.5 h

8: 0.077 g / LiAlH₄ / tetrahydrofuran; diethyl ether / 1.) room temperature, 1h, 2.) reflux, 2 h

With N-Bromosuccinimide; lithium aluminium tetrahydride; KON; hydrogen; sodium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; water; N,N-dimethyl-formamide; paraffin;

upstream raw materials:

(E)-3--1-propanol

methyl (E)--2-methylcrotonate

4-benzyloxybenzyl alcohol

3-[4-(benzyloxy)phenyl]propan-1-ol

Downstream raw materials:

4'-(3-methyl-4-hydroxybutyloxy)-3-phenylpropanol

3-(4-hydroxyphenyl)propan-1-ol

diacetylcuspidiol

Refernces

• 1、 Ishii, Hisashi,Ishikawa, Tsutomu,Tohojoh, Toshiaki,Murakami, Keiko,Kawanable, Eri,et al.. "Studies on the Chemical Constituents of Rutaceous Plants. Part 45. Novel Phenyl Propanoids: Cuspidiol, Boninenal, and Methyl Boninenalate". . p. 2051 - 2058. Retrieved 2007/10/02.