54 
and yield the acetate of cinnamic alcohol. The latter could not be 
found. 
Anethol and formaldehyde. 
One grammol. anethol is stirred with a solution of two grammol. 
formaldehyde in 30°/, sulphuric acid for three days, the product 
separated in the usual way yields, when distilled in vacuum: 
Methylene ether of p. methoxyphenylbutylglycol. 
A colourless, viscous liquid, boiling-point 168°—170° pressure 
13 mm. DF =41.1197; N’S = 1.53438. Mol. refr. 57.78 Cal. 56,74- 
It does not react with a GRIGNARD-solution at a normal temperature 
and does not decolorize a bromine-solution. 
Various efforts made to saponify the methylene ether to the cor- 
respondent glycol failed, resinification always set in or the ether 
remained unaltered. By leaving the ether for a fortnight in contact 
with 85°/, formic acid, an oil was obtained, in which such an 
amount of formic acid was chemically bound as corresponded to 
35 °/, di-formiate; saponification and distillation however, yielded an 
inconstantly boiling liquid. 
Oxydation of the methylene ether. 
In order to demonstrate, that with the anethol the formaldehyde 
had really reacted with the C=C group from the side-chain, the methy- 
lene ether was oxydized with potassium-permanganate. An acid was 
obtained with a meltingpoint of 182°—1838°, and which revealed no 
depression when mixed with anisie acid. 
Hence it appears, that in these circumstances formaldehyde does 
not react with the benzene nucleus. 
Analysis of the methylene ether: 
Hound °7.C 701,°68,2 and 69,2: Cale. for CHO, 695 
Be METRE eh. BETES Cale. fhe 
Mol. weight in benzene: found 203 and 208. Cale. as C,,H,,O,: 208. 
Isosafrol and formaldebyde. 
The condensation is effected in the same way as with the anethol. 
It gives: 
Methylene ether of 3,4 dioxymethylenephenylbutylglycol. 
Colourless, viscous liquid, boiling-point 182°—184° pressure 13 mm. 
D5, = 1,2272. Ni” — 1,54078. 
Mol.refr. 56,84. Cale. 56,18. 
Mol.weight in benzene: found 220 and 213. Cale. for C,,H,,O,: 222. 
Analysis: 
Found °/, C 64,5 and 64,8. Calc. as C,,H,,0, 64,8. 
fo 469 and. 7e. 6.3. 
