4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid

Base Information

• Chemical Name: 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid
• CAS No.: 94194-08-8
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392
• Mol file: 94194-08-8.mol

Synonyms:

Chemical Property of 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid

There total 18 articles about 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid 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:

Acetic acid 4-(1-benzyloxymethyl-4-oxo-butyl)-phenyl ester → 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid (94194-08-8)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; Yield given;

DOI:10.1248/cpb.41.1900

Reference yield:

(4-hydroxy-phenyl)-acetic acid ethyl ester (17138-28-2) → 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid (94194-08-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / diisopropylethylamine / CH₂Cl₂ / Ambient temperature

2: 1.) NaNH₂ / 1.) HMPA, ether, reflux, 1 h, 2.) HMPA, ether, reflux, 1 h

3: 95 percent / lithium aluminum hydride / diethyl ether / 1 h / Ambient temperature

4: 1.) sodium hydride, 2.) Bu₄NI / 1.) HMPA, THF, 1 h, 2.) HMPA, THF, RT, overnight

5: 87 percent / 10percent HCl / tetrahydrofuran / 6 h / Heating

6: pyridine / 0.25 h / 0 °C

7: Jones reagent / acetone / 0 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; jones reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium amide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1248/cpb.41.1900

Reference yield:

ethyl <4-(methoxy)methoxy>phenylacetate (155627-09-1) → 4-(4-acetoxyphenyl)-5-benzyloxypentanoic acid (94194-08-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaNH₂ / 1.) HMPA, ether, reflux, 1 h, 2.) HMPA, ether, reflux, 1 h

2: 95 percent / lithium aluminum hydride / diethyl ether / 1 h / Ambient temperature

3: 1.) sodium hydride, 2.) Bu₄NI / 1.) HMPA, THF, 1 h, 2.) HMPA, THF, RT, overnight

4: 87 percent / 10percent HCl / tetrahydrofuran / 6 h / Heating

5: pyridine / 0.25 h / 0 °C

6: Jones reagent / acetone / 0 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; jones reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium amide; In tetrahydrofuran; diethyl ether; acetone;

DOI:10.1248/cpb.41.1900

upstream raw materials:

(4-hydroxy-phenyl)-acetic acid ethyl ester

ethyl <4-(methoxy)methoxy>phenylacetate

4-[1,3]Dioxolan-2-yl-2-(4-methoxymethoxy-phenyl)-butan-1-ol

5-Benzyloxy-4-(4-hydroxy-phenyl)-pentanal

Downstream raw materials:

7-Benzyloxy-2-diazo-6-(4-hydroxy-phenyl)-heptan-3-one

Refernces

• 1、 Iwata, Chuzo,Morie, Toshiya,Maezaki, Naoyoshi,Shimamura, Hisafumi,Tanaka, Tetsuaki,Imanishi, Takeshi. "Stereoselective Synthesis of the B/C/D Ring Systems of Aphidicolane and Stemodane Diterpenes". . p. 930 - 932. Retrieved 2007/10/02.