Synthetic elaboration of diosphenols. Part 3. Replacement of enolic oxygen by hydrogen

The transfer of a Diels–Alder reaction of (cyclohexa-1,5-dien-1-yloxy)trimethylsilane 1 with α-acetoxyacrylonitrile 2 and acrylonitrile 8, respectively, from batch to continuous mode is presented, using standard and widely available laboratory equipment. A standard microwave-based system was used as probe for the transfer to flow reactors. Temperature and residence time have been optimized in small coiled-tube reactors and confirmed with two production runs in a flow reactor. The inherent increase in safety caused by the small volumes at high temperatures and the achieved productivity (approximately 100 g/h using acrylonitrile) are offering advantages over the batch mode which suffers from thermokinetic limitations for scale-up.

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“…1 H NMR (CDCl 3 ): 7.0 (m, 1H); 6.07 (dt, J = 10.0, ∼2.0 Hz, 1H); 2.7–1.8 (m, 6H). These values are in accordance with literature values …”

Section: Methodssupporting

confidence: 93%

“…These values are in accordance with literature values. 21 Phenol (6). 1 H NMR (CDCl 3 ): δ 7.18 (m, 2H), 6.87−6.78 (m, 3H).…”

Section: ■ Conclusionmentioning

confidence: 99%

High-Temperature Diels–Alder Reactions: Transfer from Batch to Continuous Mode

Abele

Höck

Schmidt

et al. 2011

Org. Process Res. Dev.

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“…Camphor oxime (291) reacts348 with PPA to give the usual Beckmann product together with (292)-( 295) which arise from a-campholenonitrile formed during the reaction. The oxime (296) yields the lactam (297) (36 YO) together with a mixture of campholenonitriles under Beckmann conditions.…”

Section: Camphanes and Lsocamphanesmentioning

confidence: 99%

Monoterpenoids

Grayson¹

1992

Nat. Prod. Rep.

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Introduction 2 2,6-Dimethyloctanes 3 Irregular Monoterpenoids 4 Menthanes 5 Cineol Derivatives 6 Camphanes and Isocamphanes 7 Pinanes 8 Caranes 9 Fenchanes 10 Thujanes 11 Ionone Derivatives 12 Iridanes 13 Cannabinoids I4 References NATURAL PRODUCT REPORTS, 1992-D. H. GRAYSON 533 Table 1 Plant species Abies spp. Abies alba Achillea abrotanoides Ambrosia trcfida A r t em isia scoparia Bidens pilosa Buddleia sal vifolia Cestrum nocturnum Chaerophyllum bulbosum spp. Citrus aurantium var. Citrus limoniu var. Osbeck Comptonia peregrina Cymbopogon distans f. Drucocephalum moldavica Elettaria cardamomum Maton. Elsholtzia blanda E. pilosa E. polysracha E. stauntonii Eucalyptus Pscerta Feronia limonia Fil ipendula ulniar ia Fissistigma shangtzeense Gutierrezia surothrae Hyp t is pee tinu ta H . suaveolens Poit. Hyssopus oficinalis Illicium simonsii Juniperus recurvata var. Levisticum ojicinale Lomatium grayi Melaleuca alternjfolia Melissa oficinalis Mentha arvensis Mercurialis Ieiocarpa Micromeria teneriflae Benth. Momordica charantia Monodoru myristica Murraya spp. M . k wangsiensis Ocimum basilicum 0 lear ia p h logo pap pa Origanum mujorana 0. onites Picea abies Karst. Pinus cretacea Kollenicz. Piper nigrum Ribes nigrum Ribes nigrum Rosa cymosa Salvia lavandulaefolia sspp.

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