1-(2-Hydroxyphenyl)-3-methylbutan-1-one

Base Information

• Chemical Name: 1-(2-Hydroxyphenyl)-3-methylbutan-1-one
• CAS No.: 19019-21-7
• Molecular Formula: C11H14 O2
• Molecular Weight: 178.231
• NSC Number: 115702
• DSSTox Substance ID: DTXSID10297363
• Nikkaji Number: J852.605B
• Wikidata: Q82038420
• Mol file: 19019-21-7.mol

Synonyms:1-(2-hydroxyphenyl)-3-methylbutan-1-one;19019-21-7;1-Butanone, 1-(2-hydroxyphenyl)-3-methyl-;o-Isovalerylphenol;NSC115702;DTXSID10297363;NSC-115702;A19282

Chemical Property of 1-(2-Hydroxyphenyl)-3-methylbutan-1-one

Chemical Property:

• Vapor Pressure: 0.00595mmHg at 25°C
• Boiling Point: 264.4°C at 760 mmHg
• Flash Point: 109.9°C
• PSA: 37.30000
• Density: 1.052g/cm³
• LogP: 2.62100
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)C1=CC=CC=C1O

Technology Process of 1-(2-Hydroxyphenyl)-3-methylbutan-1-one

There total 19 articles about 1-(2-Hydroxyphenyl)-3-methylbutan-1-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: 92.0%

2-[3-methyl-1-((1R)-1-phenylethyl)iminobutyl] phenol → 1-(2-hydroxyphenyl)-3-methylbutan-1-one (19019-21-7)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 40 ℃; for 4h;

DOI:10.1016/S0040-4020(98)00985-5

Reference yield: 91.0%

salicylonitrile (611-20-1) + Isobutyl bromide (78-77-3) → 1-(2-hydroxyphenyl)-3-methylbutan-1-one (19019-21-7)

Guidance literature:

Isobutyl bromide; With magnesium; In tetrahydrofuran; for 2h; Reflux;

salicylonitrile; In tetrahydrofuran; for 2h; Reflux;

With sulfuric acid; water; In tetrahydrofuran; at 80 ℃; for 1h; Cooling with ice;

DOI:10.1371/journal.pone.0112059

Reference yield: 67.0%

N,N-diethylsalicylamide (19311-91-2) + (2-methylpropyl)diphenylchlorosilane (81851-76-5) → 1-(2-hydroxyphenyl)-3-methylbutan-1-one (19019-21-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1002/anie.201404495

upstream raw materials:

isopentanoyl chloride

phenol

phenyl 3-methylbutanoate

2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one

Downstream raw materials:

(3-methyl-butyl)-phenol

(Z)-3-(2-methylpropylidene)phthalide

(4R)-4-isobutyl-3-[(1R)-1-phenylethyl]-3,4-dihydro-2H-1,3-benzoxazine

2-<(1R)-3-methyl-1-(<(1'R)-1'-phenylethyl>amino)butyl>phenol

Refernces

• 1、 Hu, Le' an,Zhang, Yao,Zhang, Qing-Wen,Yin, Qin,Zhang, Xumu. "Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2". supporting information. p. 5321 - 5325. Retrieved 2020/02/28.
• 2、 Potuckova, Eliska,Hruskova, Katerina,Bures, Jan,Kovarikova, Petra,Spirkova, Iva A.,Pravdikova, Katerina,Kolbabova, Lucie,Hergeselova, Tereza,Haskova, Pavlna,Jansova, Hana,Machacek, Miloslav,Jirkovska, Anna,Richardson, Vera,Lane, Darius J. R.,Kalinowski, Danuta S.,Richardson, Des R.,Vavrova, Katerina,Simunek, Tomas. "Structure-activity relationships of novel salicylaldehyde isonicotinoyl hydrazone (SIH) analogs: Iron chelation, anti-oxidant and cytotoxic properties". . . Retrieved 2015/02/19.