65383-62-2

Usage

Uses

Used in Fragrance and Flavor Industry:
2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE is used as a fragrance and flavoring agent for its sweet and floral scent, adding pleasant aromas to various products such as perfumes, cosmetics, and food items.
Used in Medicinal Applications:
2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE is used as a potential therapeutic agent for its antioxidant and anti-inflammatory properties, which may contribute to the treatment or management of various health conditions.
Used in Cosmetic Applications:
2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE is used as an ingredient in cosmetic products for its antioxidant and anti-inflammatory properties, which may help improve skin health and provide protective effects against environmental stressors.

InChI:InChI=1/C14H18O4/c1-5-17-13-7-11-9(6-12(13)16-4)10(15)8-14(2,3)18-11/h6-7H,5,8H2,1-4H3

Upstream product

• 118948-74-6 7-ethoxy-6-hydroxy-2,2-dimethyl-4-chromanone 
• 74-88-4 methyl iodide 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 533-31-3 Sesamol 
• 112979-30-3 3,4-dioxymethylene phenyl 3-methyl-2-butenoate 
• 112979-31-4 1-(2-hydroxy-4,5-methylenedioxyphenyl)-3-methyl-2-buten-1-one 
• 73673-87-7 2,2-dimethyl-6,7-methylenedioxy-4-chromanone 
• 118948-72-4 1-(2',4',5'-trihydroxyphenyl)-3-methyl-1-oxo-2-butene 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 541-47-9 3-Methylbutenoic acid 
• 76348-95-3 2,2-Dimethyl-6,7-dihydroxy-4-chromanone 
• 65383-57-5 3-ethoxy-4-methoxy phenol 

Downstream Products

• 65383-73-5 6-methoxy-7-ethoxy-2,2-dimethyl-2H-chromene 
• 86778-15-6 7-ethoxy-2,2-dimethyl-6-methoxy-8-(2',5',8'-trioxadodecyl)chromene 
• 86778-13-4 7-ethoxy-2,2-dimethyl-6-methoxy-8-(2',5',8',11'-tetraoxadodecyl)chromene 

Relevant academic research and scientific papers

An efficient synthesis of 2,2-dimethyl-4-chromanones

Chromanones are obtained in high yields by treating substituted phenols with dimethyl acrylic acid in the presence of trifluoroacetic acid.

A NEW SYNTHESIS OF PRECOCENE II AND PRECOCENE III BASED ON THE PHOTO-FRIES REARRANGEMENT OF A SESAMOL ESTER

The photo-Fries rearrangement of the sesamol ester of 3-methylcrotonic acid (2) in the presence of potassium carbonate affords a mixture of the o-hydroxyketones (3c) and (3d).Basic cyclization of the latter leads to the chromanones (4c) or (4d), respectively.Treatment of 4c with alkoxide/alcohol results in the regioselective cleavage of the methylenedioxy ring, to give the corresponding 7-alkoxy derivatives (4e) or (4f).Subsequent methylation with methyl iodide gives to rise to 4a or 4b and final reduction/dehydration by conventional methods affords the target compounds Precocene II (1a) or Precocene III (1b).

Chromene derivatives and pesticidal composition comprising the same

The invention relates to a process for the preparation of chromenes of the general Formula V STR1 (wherein R1 and R2 are hydrogen, optionally halogeno substituted C1-6 alkyl or aryl; R3 and R7 stand for hydrogen, halogen or C1-6 alkyl; R4 represents C1-8 alkyl, aryl, aralkyl or a group containing a carbonyl group; R5 and R6 stand for C1-10 alkyl, aryl, amino, hydroxyalkyl, alkoxyalkenyl, alkylmercaptoalkyl, acyl, carboxy or an ester group or a halogen atom; n is 0 or 1) which comprises (a) for the preparation of compounds, in which R5 and R6 stand for different groups, reacting a compound of the general Formula I STR2 with an approximately equimolar, preferably 0.8-1.5 molar amount of a reactant of the general Formula R5 --X-related to the amount of the compound of the general Formula I (wherein R5 has the same meaning as stated above X is halogen) and reacting the O-monosubstituted compound of the general Formula III STR3 (wherein R1 -R6 and n are as stated above) obtained with a 1.1-1.5 molar amount of a compound of the general Formula III (wherein R6 and X are as stated above); or (b) for the preparation of compounds, in which R5 and R6 stand for the same group, reacting a chromanone of the general Formula I (wherein R1 -R4 and m have the meaning as stated above) with a 2-3 molar amount of a compound of the general Formula R5 --X-related to the amount of the compound of the general Formula I (wherein R5 and X are as stated above), preferably in the presence of a base, a catalyst and a solvent, and thereafter reducing the O-substituted chromanone derivative of the general Formula III thus obtained (wherein R1 -R6 and n are as stated above) and dehydrating the chromanol derivative of the general Formula IV STR4 thus obtained (wherein R1 -R6 and n are as stated above) in acidic-aqueous medium. The compounds of the general Formula V are partly new and useful for the preparation of pesticides.

A Novel Synthesis of Precocenes. Efficient Synthesis and Regioselective O-Alkylation of Dihydroxy-2,2-dimethyl-4-chromanones

The reactions of trihydroxybenzenes 1a-c and 3-methylbut-2-enoic acid (2) in a zinc chloride/water/phosphoryl chloride system afford either the new trihydroxyphenylbutenone derivatives 3b,c or dihydroxy-2,2-dimethyl-4-chromanones 4a-c in good yields.Compounds 3b,c can be cyclized in high yields to 4b,c in 5percent sodium hydroxide solution.Regioselective O-alkylation of 4a-c leads to 5a-f in good yields.O-Alkylation of 5a-f, followed by reduction and dehydration, results in the formation of precocene 3 (7d) and its regioisomer 7a-c,e,f.Methylation of 4a-c gives 6g-i.Subsequent reduction and dehydration affords precocene 2 (7h) and its regiosiomers 7g,i.