from water. 
cat oxylate (V) is brought, in benzene solution, to react with zinc and ethyl bromo- 
ed, according to Willstatter, in ethereal solution with platinum black and hydrogen. 
ar isomeric acid seems to be present which crystallizes more difficultly. 
~amphor. (XI), a liquid, the semicarbazone of which melts at 210 to 211°. Methyl- 
camphor was brought into reaction with methyl iodide and sodium amide in absolute- 
th osctantt aay cn regenerated therefrom was a liquid with a smell of fenchone; 
oxime, m.p. 98 ‘to 99°, ene See é 
; "The: r-fenchone (XIV) distilled off fei the semicarbazone of fechecanren one howled’ 
xim from fennel oil and l-fenchone oxim from thuja oil) no Gepiescion of the melting point. 
H.C: CO- CHe- CH, - CO, C.Hs as ‘CH: Br: ae Cy Hs a One fost 
(I) Ethyl Pyare . : 
i) SrLnY |’ ; | CN 
CH, CO.- ‘CoH 7 CH,- CO, CG Hs 
) Lactone of monoethyl-2-methyl-2-hydroxy- eee — (U1) Diethyl Someiiylee-ey ano 4- butane- sre 
__-_ adipate. dicarboxylate. 
| CO2C H, 
Very 220I5 
» 
fe His «CH, “CHy COnCsHs ee Nan ce th 
CH:: -CO.CzHs eed 
(IV) Triethyl semethyl-1, 2, butane tricarboxylate. eee eee An eae 
Ne, CHs j * : } é ve CH; 
lan CO:CHs 4 me con 
On distilling t the lead salt ae 
% ou or r preparing ethyl Sen sebnieitighort omo camphorate (IX) ethyl Pipe Meare ing 
te. The product resulting is a mixture of the dehydro ester (IX) and the hydroxy hat i 
(X). In order to transform the mixture entirely into the unsaturated ester itis 
with phosphorus trichloride in chloroform solution. , The dehydro ester:is: then.” 
resulting ethyl methylnorhomocamphorate (XI) boils from 147 to 1499 (14 mm). 
free acid, after recrystallization from water, melts from 116 to 118°. In addition, aa 
The lead salt of methylnorhomocamphoric acid yields on dry distillation methyl. ie 
real re aeaete The reaction- product, freed from excess of oak Se and solvent, ae 
é to- 73° (12 mm.). The | oxime, m.p. 158 to 159°, showed after mixing with the — 5, 
qu al amount of (d + ))-fenchone oxime, m.p. 158 to 159° (prepared from d-fenchone oe Ve : 
OF SN 
/ , 
Vey Nay 
HAC. -C-CH,- CH:- co + KCN —> — HAC. C-CH,-CHb- COsC, ee 
, CH, 3 + Ethyl « o-bromoiso- = SA HE i Bs ; 4+<PBre 
“g ee ; Ls | butyrate He “Aroha a CO C, Hs. 
a? - eee aS oS mee 
eee COs Shires ies a _  C-OH 
Eth yl A-methyi2-keto-1ayclopentane . Sh - (VI) Ethyl hydroxy- 
be. _ carboxylate. ee eter ok boeh homofenchonate. 
