Methyl sesamol

Hydroxy- J-qidnones Silver oxide oxidizes derivatives of methyl sesamol 1 to quinones of this type (equation 1). 

Methyl sesamol, 353, 354 3-Methylsulfonyl-2,5-dihydrofurane, 270 Methylthiotrimethylsilane, 113 Methyltitanium trichloride, 270-271 (S)-(—)-Methyl p-toluenesulfinate, 405 l-Methyl-2-trimethylsiloxy-l, 3-butadiene, 271-272... 

SYNTHESIS A solution of 11.5 g pellet KOH (85%) in 75 mL EtOH was treated with 25 g sesamol followed by 27 g methyl iodide. This was brought to reflux on the steam bath. Salt formation was apparent in 20 min, and refluxing was maintained for atotal of 4 h. The solvent was removed under vacuum, and residue poured into 400 mL H,0. This was acidified with HC1 and extracted with 3x150 mL... 

The remaining MMDA-analogue that has been prepared, is the 2,3,6-isomer. The flow diagram started with sesamol (3,4-methylenedioxyphenol) which was methylated with methyl iodide, converted to the aldehyde using butyllithium and N-methylformanilide (putting the new group directly between the two oxygen... 

Two other interesting reports on IMFIDA reactions describe the application of solvent-free, solid-support catalyzed microwave technology. Indeed, as mentioned previously in Scheme 11.2, the IMHDA reaction for synthesis of octahydroacridine 6 was efficiently catalyzed by Si02/ZnCl2 under microwave irradiation conditions [36]. In another example (Scheme 11.10), sesamol 31 and 3-methyl-2-butenal 32 reacted to provide 35, under basic KIO-K clay-catalyzed solvent-free microwave conditions. The IMHDA reaction of o-quinone methine 34 produced the expected chromene 35 in 84% yield within 8 min. Conventional heating conditions at 110 °C (K10-K+, 60 min) were longer and provided the desired product 35 in an equivalent 91% yield but with 9% of another, unidentified product (Scheme 11.10) [34b]. 

A solvent-free procedure for the preparation of methylenedioxyprecocene (MDP), a natural insecticide, has been developed for use in the undergraduate organic chemistry laboratory a section of 15 students is being used as a test group. The synthesis involves, in tandem, electrophilic addition of 3-methyl-2-butenal to sesamol, followed by dehydration and an intramolecular hetero-Diels-Alder cyclization (Scheme 6.6). Montmorillonite-KlO, a commercially available basic clay, is used as a support... 

Phenol, 3,4-(methylenedioxy). See Sesamol Phenol, 2,2 -((1-methyl-1,2-ethanediyl) bis (nitrilomethylidyne)) bis-. SeeN,N -Disalicylidene-1,2-propanediamine Phenol methyl ether. See Anisole Phenol, 2-(1-methylethyl)-. Seeo-Isopropylphenol... 

Methyl gallate Ethyl gallate Propyl gallate Butyl gaUate Octyl gaUate Dodecyl gaUate BHA BHT Sesamol NDGA... 

Following the classical syntheses of aromatic a-sialosides by phase transfer catalysis starting with the per-O-acetylated sialosyl chloride methyl ester, further aromatic a-sialosides could be prepared with sesamol (4), 2-chloro -nitrophenol (5), and 4-chloro-5-methyl-4-nitrophenol (6) [36]. In TcTS-sialylations none of these modified donor substrates showed any sialylation of methyl p-lactoside (7) to give the methyl sialyllactoside (8). It may be assumed that both steric and electronic factors affect interactions with aromatic and/or hydrophobic amino acid residues in the enzyme (Scheme 1). 

Also obtained by reaction of acetyl chloride with sesamol methyl ether (b.p.,g 110-114°) in the presence of aluminium chloride in ethyl ether at r.t. overnight (36%) [2504],... 

---