6-Hydroxy-2,2-dimethylchroman-4-one

Base Information

• Chemical Name: 6-Hydroxy-2,2-dimethylchroman-4-one
• CAS No.: 31366-85-5
• Molecular Formula: C11H12O3
• Molecular Weight: 192.21
• Hs Code.: 2914400090
• DSSTox Substance ID: DTXSID70393259
• Nikkaji Number: J88.721H
• Wikidata: Q82191966
• ChEMBL ID: CHEMBL1384267
• Mol file: 31366-85-5.mol

Synonyms:31366-85-5;6-HYDROXY-2,2-DIMETHYLCHROMAN-4-ONE;6-hydroxy-2,2-dimethyl-3H-chromen-4-one;2,2-DIMETHYL-6-HYDROXY-4-CHROMANONE;6-hydroxy-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one;6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one;SMR000132431;MLS000522023;MFCD03830209;HMS1646M17;Opera_ID_1082;SCHEMBL1146916;CHEMBL1384267;DTXSID70393259;UAXWPLCLDSMHRF-UHFFFAOYSA-N;HMS2529K06;AR2690;NSC804055;2,2-dimethyl-6-hydroxychroman-4-one;AKOS002130568;AS-9366;NSC-804055;6-Hydroxy-2,2-dimethyl-chroman-4-one;SY088356;CS-0061117;FT-0717882;EN300-193176;A919190;6-hydroxy-2,2-dimethyl-2,3-dihydrobenzopyran-4-one;F0918-7088;Z1198163333

Chemical Property of 6-Hydroxy-2,2-dimethylchroman-4-one

Chemical Property:

• Melting Point: 159 °C
• Boiling Point: 354.3±42.0 °C(Predicted)
• PKA: 9.59±0.40(Predicted)
• PSA: 46.53000
• Density: 1.196±0.06 g/cm3(Predicted)
• LogP: 2.13600
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 192.078644241
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

98%Min ^*data from raw suppliers

6-Hydroxy-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC(=O)C2=C(O1)C=CC(=C2)O)C

Technology Process of 6-Hydroxy-2,2-dimethylchroman-4-one

There total 16 articles about 6-Hydroxy-2,2-dimethylchroman-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: 89.0%

acetone (67-64-1) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-hydroxy-2,2-dimethyl-chroman-4-one (31366-85-5)

Guidance literature:

With piperidine; for 0.166667h; Neat (no solvent); Microwave irradiation;

Reference yield: 83.0%

2,5'-dihydroxy acetophenone (131341-58-7) + acetone (67-64-1) → 6-hydroxy-2,2-dimethyl-chroman-4-one (31366-85-5)

Guidance literature:

With pyrrolidine; In acetonitrile; at 40 ℃; for 18h; Inert atmosphere;

DOI:10.1002/chem.201002757

Reference yield: 72.0%

2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one (3780-33-4) → 6-hydroxy-2,2-dimethyl-chroman-4-one (31366-85-5)

Guidance literature:

2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one; With [bis(acetoxy)iodo]benzene; trifluoroacetic acid; at 0 - 20 ℃; for 0.5h; Reflux;

With water; at 120 ℃; regioselective reaction;

DOI:10.1039/c7cc08588e

upstream raw materials:

1-(2,5-dihydroxyphenyl)-3-methyl-2-buten-1-one

1-(2',5'-dihydroxyphenyl)-1-oxo-3-methylbutane-3-ol

acetone

2,5-Dihydroxyacetophenone

Downstream raw materials:

4-(tert-butyldiphenylsiloxy)-2,2-dimethyl-6-(2'-methylbut-3'-en-2'-yloxy)chromane

4-(tert-butyldiphenylsiloxy)-2,2-dimethyl-5-(3'-methylbut-2'-enyl)chroman-6-ol

4-(tert-butyldiphenylsiloxy)-2,2-dimethyl-7-(3'-methylbut-2'-enyl)chroman-6-ol

6-benzyloxy-2,2-dimethyl-7-(3'-methylbut-2'-enyl)chroman-4-one

Refernces

• 1、 El-Desoky,Badria,Abozeid,Kandeel,Abdel-Rahman. "Synthesis and antitumor studies of novel benzopyrano-1,2,3-selenadiazole and spiro[benzopyrano]-1,3,4-thiadiazoline derivatives". . p. 2105 - 2114. Retrieved 2013.
• 2、 Viswanadh,Ghotekar, Ganesh S.,Thoke, Mahesh B.,Velayudham,Shaikh, Aslam C.,Karthikeyan,Muthukrishnan. "Transition metal free regio-selective C-H hydroxylation of chromanones towards the synthesis of hydroxyl-chromanones using PhI(OAc)2 as the oxidant". supporting information. p. 2252 - 2255. Retrieved 2018/03/06.