37847-35-1

Basic information

• Product Name: Ethanone, 1-[4-hydroxy-2-methyl-5-(1-methylethyl)phenyl]-
• Synonyms: 4-acetyl-2-isopropyl-5-methylphenol;1-(4-Hydroxy-5-isopropyl-2-methyl-phenyl)-aethanon;Ethanone,1-[4-hydroxy-2-methyl-5-(1-methylethyl)phenyl];4'-HYDROXY-5'-ISOPROPYL-2'-METHYLACETOPHENONE;4-hydroxy-5-isopropyl-2-methylphenyl methyl ketone;1-(4-hydroxy-5-isopropyl-2-methylphenyl)ethanone;4-Acetyl-thymol;1-[4-hydroxy-2-methyl-5-(propan-2-yl)phenyl]ethan-1-one
• CAS NO: 37847-35-1
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• Mol File: 37847-35-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152–154°C
• CAS DataBase Reference: Ethanone, 1-[4-hydroxy-2-methyl-5-(1-methylethyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[4-hydroxy-2-methyl-5-(1-methylethyl)phenyl]-(37847-35-1)
• EPA Substance Registry System: Ethanone, 1-[4-hydroxy-2-methyl-5-(1-methylethyl)phenyl]-(37847-35-1)

Safety Data

• Hazardous Substances Data: 37847-35-1(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetyl chloride on thymol, with aluminium chloride, in nitrobenzene or with zinc chloride.

Upstream product

• 528-79-0 2-isopropyl-5-methylphenyl acetate 
• 38031-61-7 1-(5-isopropyl-4-methoxy-2-methyl-phenyl)-ethanone 
• 89-83-8 thymol 
• 75-36-5 acetyl chloride 
• 1076-56-8 Thymol methyl ether 

Downstream Products

• 584-44-1 p-thymotic acid 
• 102162-05-0 1-(3-benzyl-4-hydroxy-5-isopropyl-2-methyl-phenyl)-ethanone 
• 87816-63-5 2,4-Dibenzyl-6-isopropyl-3-methyl-phenol 
• 132948-33-5 1-(4-Hydroxy-5-isopropyl-2-methyl-3-pyrrolidin-1-ylmethyl-phenyl)-ethanone 
• 132948-32-4 1-(4-Hydroxy-5-isopropyl-2-methyl-3-piperidin-1-ylmethyl-phenyl)-ethanone 
• 132948-44-8 1-{3-[4-(3-Acetyl-6-hydroxy-5-isopropyl-2-methyl-benzyl)-piperazin-1-ylmethyl]-4-hydroxy-5-isopropyl-2-methyl-phenyl}-ethanone 
• 132948-31-3 1-[4-Hydroxy-5-isopropyl-2-methyl-3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-ethanone 
• 126570-36-3 2-Isopropyl-4-hydroxyisopropyl-5-methylphenol 
• 132948-45-9 1-{3-[4-(3-Acetyl-6-hydroxy-5-isopropyl-2-methyl-benzyl)-2,5-dimethyl-piperazin-1-ylmethyl]-4-hydroxy-5-isopropyl-2-methyl-phenyl}-ethanone 
• 528-79-0 2-isopropyl-5-methylphenyl acetate 
• 110784-97-9 1-[5-isopropyl-2-methyl-4-(2-piperidinoethoxy)phenyl]ethan-1-one 
• 132948-68-6 1-{5-isopropyl-2-methyl-4-[2-hydroxy-3-piperidinopropoxy}phenyl]ethan-1-one 
• 518291-07-1 1-{5-isopropyl-2-methyl-4-[2-hydroxy-3-(pyrrolidin-1-yl)propoxy}phenyl]ethan-1-one 
• 518291-06-0 1-{5-isopropyl-2-methyl-4-[2-hydroxy-3-morpholinopropoxy}phenyl]ethane-1-one 

Relevant articles and documents

Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene

Thymoquinone was recently reported as having a unique pencil-like odor and being the impact compound for the cedar-like and cedar wood-based product smell such as pencils. The compounds thymol and carvacrol are structurally related odorants commonly found in plants and foods such as thyme and oregano, also having a significant contribution to their overall aroma. However, a systematic elucidation of the sensory properties in this class of oxygenated, aromatic monoterpenoids has not been carried out. To close this gap and gain new insights into structure-odor relationships leading to pencil-like and woody odors, 19 structurally related derivatives of p-cymene starting from thymol and carvacrol were synthesized and characterized. The compounds had odor thresholds ranging from 2.0 ng/L air to 388.8 ng/L air, being lowest for thymol and carvacrol and highest for thymohydroquinone. The compounds smelled mostly thyme-like, oregano-like, and pencil-like with phenolic, earthy, and medicinal variations in their odor character, which could be successfully linked to structural motifs.

Regioselective fries rearrangement and friedel-crafts acylation as efficient routes to novel enantiomerically enriched ortho-acylhydroxy[2.2]paracyclophanes

Two useful approaches to ortho-acylhydroxy[2.2]paracyclophanes, starting from 4-hydroxy[2.2]paracyclophane, have been developed. TiCl4-catalyzed Fries rearrangement and direct acylation occur regioselectively (to the ortho position with respect to the hydroxy group), leading to 4-acetyl-5-hydroxy[2.2]paracyclophane (3) and 4-benzoyl-5-hydroxy[2.2]-paracyclophane (4) in high to excellent chemical yields. For compound 4, an X-ray investigation has been performed. ortho-Acylhydroxy[2.2]paracyclophanes 3 and 4 have been obtained in enantiomerically enriched forms (ee 92-99%) and the absolute configurations of their enantiomers have been determined.

Photo-Fries Rearrangement: Synthesis of Alkyl Hydroxyaryl Ketones

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