تفاعل #5113

ord-e0f6b927331840ff8925668d568d22be

معادلة التفاعل

Cc1cc(OCCOCC2CC2)ccc1O
4-(2-(cyclopropylmethoxy)ethoxy)-2-methylphenol
ClCC1CO1
epichlorhydrin
C1CCNCC1
piperidine
BrCC1CC1
cyclopropylmethyl bromide
Cc1cc(OCCOCC2CC2)ccc1OCC1CO1
2-methyl-1-(2,3-epoxypropoxy)-4-(2-(cyclopropylmethoxy)ethoxy)benzene

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

The epoxide starting material is obtained from reaction of 4-hydroxy-3-methylphenyl benzoate with benzyl bromide to give 4-benzyloxy-3-methylphenyl benzoate (M.P. 120°-121° from methanol/ether), followed by de-esterification with 2M NaOH solution to give 4-benzyloxy-3-methylphenol (M.P. 69°-70° from ether/hexane) and reaction with 2-bromoethanol (light brown oil) to form an alcohol which is reacted with cyclopropylmethyl bromide in tetrahydrofuran. Debenzylation of the cyclopropylmethoxyethoxy derivative (unpurified) with 10% Pd on activated charcoal forms 4-(2-(cyclopropylmethoxy)ethoxy)-2-methylphenol which is then reacted with epichlorhydrin in the presence of a catalytic amount of piperidine to give 2-methyl-1-(2,3-epoxypropoxy)-4-(2-(cyclopropylmethoxy)ethoxy)benzene (light brown oil after chromatography on silica gel with toluene/ethyl-acetate (8:2)).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05242943uspto-grants-1993_09