4-Hydroxy-2-tetradecenal

Base Information

• Chemical Name: 4-Hydroxy-2-tetradecenal
• CAS No.: 81335-92-4
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.359
• Nikkaji Number: J346.179C
• Mol file: 81335-92-4.mol

Synonyms:4-hydroxy-2-tetradecenal

Chemical Property of 4-Hydroxy-2-tetradecenal

Chemical Property:

• PSA: 37.30000
• LogP: 3.63320
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 226.193280068
• Heavy Atom Count: 16
• Complexity: 176

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(C=CC=O)O
• Isomeric SMILES: CCCCCCCCCCC(/C=C/C=O)O

Technology Process of 4-Hydroxy-2-tetradecenal

There total 10 articles about 4-Hydroxy-2-tetradecenal 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: 76.0%

4-(2-hydroxyethyl)-5-decyl-1,3-dioxolan-2-one → (E)-4-hydroxytetradec-2-enal (81335-92-4)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; for 4h; stereoselective reaction; Inert atmosphere; Reflux;

DOI:10.1002/asia.201900421

Reference yield:

Dodecanal (112-54-9) → (E)-4-hydroxytetradec-2-enal (81335-92-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: piperdinium acetate / dimethyl sulfoxide / 100 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 °C / Reflux

3.1: potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 °C

4.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

4.2: 0.67 h / 20 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux

With pyridine; potassium osmate(VI) dihydrate; lithium aluminium tetrahydride; methanesulfonamide; piperdinium acetate; potassium carbonate; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; tert-butyl alcohol;

DOI:10.1002/asia.201900421

Reference yield:

1-dodecyl alcohol (112-53-8) → (E)-4-hydroxytetradec-2-enal (81335-92-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: piperdinium acetate / dimethyl sulfoxide / 100 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 °C / Reflux

4.1: potassium hexacyanoferrate(III); potassium carbonate; potassium osmate(VI) dihydrate; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 °C

5.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

5.2: 0.67 h / 20 °C / Inert atmosphere

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Inert atmosphere; Reflux

With pyridine; potassium osmate(VI) dihydrate; lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; piperdinium acetate; potassium carbonate; dimethyl sulfoxide; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; tert-butyl alcohol;

DOI:10.1002/asia.201900421

upstream raw materials:

Acetic acid 1-((E)-3-oxo-propenyl)-undecyl ester

Acetic acid 1-((E)-3-hydroxy-propenyl)-undecyl ester

(E)-1-(Tetrahydro-pyran-2-yloxy)-tetradec-2-en-4-ol

Dodecanal

Downstream raw materials:

2-decylfuran

Refernces

• 1、 Iriye,Konishi,Uno,Ohwa. "Synthesis of 4-hydroxy-2-alkenals and 4-oxo-2-alkenols from 4-tetrahydropyranyloxy-2-butenal and their antimutagenic effect against UV-induced Escherichia coli WP2 B/r Trp-.". . p. 1303 - 1305. Retrieved 2007/10/02.