6-Hydroxy-2-methyl-6-p-tolylhept-2-en-4-one

Base Information

• Chemical Name: 6-Hydroxy-2-methyl-6-p-tolylhept-2-en-4-one
• CAS No.: 113283-35-5
• Molecular Formula: C15H20O2
• Molecular Weight: 232.323
• DSSTox Substance ID: DTXSID30550841
• Mol file: 113283-35-5.mol

Synonyms:113283-35-5;6-hydroxy-2-methyl-6-p-tolylhept-2-en-4-one;6-Hydroxy-2-methyl-6-(p-tolyl)hept-2-en-4-one;6-Hydroxy-2-methyl-6-(4-methylphenyl)hept-2-en-4-one;DTXSID30550841

Chemical Property of 6-Hydroxy-2-methyl-6-p-tolylhept-2-en-4-one

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(C)(CC(=O)C=C(C)C)O

Technology Process of 6-Hydroxy-2-methyl-6-p-tolylhept-2-en-4-one

There total 10 articles about 6-Hydroxy-2-methyl-6-p-tolylhept-2-en-4-one 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: 50.0%

2,4-Dihydroxy-2-(p-tolyl)-6-methyl-hept-5-ene (75136-34-4) → 2-Hydroxy-2-(p-tolyl)-6-methylhept-5-en-4-one (113283-35-5)

Guidance literature:

With jones' reagent; In acetone;

Reference yield:

4-methyl-pent-3-en-2-one (141-79-7) + para-methylacetophenone (122-00-9) → 2-Hydroxy-2-(p-tolyl)-6-methylhept-5-en-4-one (113283-35-5)

Guidance literature:

With cerium(III) chloride; lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF;

DOI:10.1016/S0040-4039(00)96393-7

Reference yield:

ethyl (4-methylbenzoyl)acetate (27835-00-3) → 2-Hydroxy-2-(p-tolyl)-6-methylhept-5-en-4-one (113283-35-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / p-TosOH / benzene / Heating

2: 70 percent / LiAlH₄ / diethyl ether / 2.5 h / Heating

3: 54 percent / pyridinium chlorochromate/NaOAc / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 1. Mg / 1. THF 2. THF/room temperature/overnight, then 2 h/reflux

5: 77 percent / aq. HCl / acetone / 2 h

6: 1. Mg / 1. Et₂O 2. Et₂O/room temperature/overnight

7: 50 percent / Jones' reagent / acetone

With hydrogenchloride; lithium aluminium tetrahydride; jones' reagent; sodium acetate; magnesium; pyridinium chlorochromate; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; acetone; benzene;

upstream raw materials:

2,4-Dihydroxy-2-(p-tolyl)-6-methyl-hept-5-ene

4-methyl-pent-3-en-2-one

para-methylacetophenone

2-(4-tolyl)-2-(trimethylsiloxy)propanenitrile

Downstream raw materials:

(+/-)-ar-turmerone

(S)-turmeronol A

(E)-6-methyl-2-(p-tolyl)hept-2-en-4-one

(+)-(S)-ar-turmerone