Reaction #82446

Reaction equation

tert-butyl (3-methyl-6-carbomethoxy-2-cyclohexen-1-yl)-carbamate

→

tert-butyl 3-methyl-6-carboxy -2-cyclohexen-1-yl-carbamate

Yield 74.0%

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   Otherhas formed
2. 2
   ExtractionThe solution is extracted once using diethyl ether
3. 3
   Otheris then established at 0° C.
4. 4
   ExtractionAfter the mixture has been extracted
5. 5
   Otherevaporated

Procedure

5 g (18.6 mmol) of tert-butyl (3-methyl-6-carbomethoxy-2-cyclohexen-1-yl)-carbamate are introduced into 40 ml of 1N sodium hydroxide solution, and the mixture is stirred at 50° C. until a clear solution has formed. The solution is extracted once using diethyl ether, and a pH of 1 is then established at 0° C. using concentrated hydrochloric acid. After the mixture has been extracted using diethyl ether and evaporated, 3.5 g (74% of theory) of tert-butyl 3-methyl-6-carboxy -2-cyclohexen-1-yl-carbamate of melting point 132°-136° C. are obtained. ##STR77## (Process B/a)

Source