Methyl perillate

Devon and Scott s Handbook91) essential oil from Salvia dorisiana92 contains perillyl acetate and the rare methyl perillate (34 R = C02Me) tricyclene is present in Agathis australis as a major component,93 and ds-carveyl acetate is a major component in Japanese spearmint (Mentha spicata crispa).94 Some rare oxygenated menthanes have been isolated from Mentha gentilis,95 and from Piper nigrum.96... 

Bardyshev reports the salicylic acid-catalysed rearrangement of isoterpinolene to various p-methadienes (cf. Vol. 3, p. 71, ref. 314). Lewis acid-catalysed rearrangement of methyl perillate is reported in an investigation of the acylation of the exocyclic double bond. " Pyrolysis of limonene diacetate yields perillyl acetate as the major product. ... 

When perillic acid is dissolved in five times its weight of amyl alcohol and is reduced by sodium at the boiling temperature, dihydro-perillic acid, CjoH Oj, is obtained. This acid melts at 107° to 109° C. By the reduction of its methyl ester by means of sodium, dihydroperillic alcohol is fornned, which is a liquid with a rose odour and having the following characters —... 

Recombination of the intermediate methyl radical (at position 17) with 52 provides benzoate ester 56 and regeneration of the cop-peril) bromide. This reaction is also known as a Kfuimsch oxidation.19... 

Peril uoro-fc /V-butyI methyl sulfide was synthesized by treatment of the silver derivative with trifluoromethylsulfenyl chloride. The disulfide was also obtained from initial reaction with elemental sulfur, followed by treatment with the sulfenyl chloride (Scheme 1.13).43... 

Alcohols can be O-methylated with diazomethane in the presence of a protic acid such as fluoroboric acid 210 Meerwein and Hinz211 showed that zinc chloride was an effective catalyst in 1930 and trifluoroborane later found favour 212 An alcohol adsorbed onto neutral silica gel undergoes O-methylation213 and the method can be used on a moderate scale [Scheme 4.117]214 though the perils of preparing diazomethane on a moderate scale must be the cause of some trepidation When tin(Il) chloride is used as the catalyst selective mono-0-methyla-tion of a l 2-diol can be achieved [Scheme 4 118] 215... 

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