Reaction #2329069

Reaction equation

hydrochloric acid

water

sodium

4-(2,2-dimethyl-2,3-dihydrobenzo[2,3-b]furan-7-yloxy)butyl acetate

→

subject compound

Yield 84.6%

4-(2,2-dimethyl-2,3-dihydrobenzo[2,3-b]furan-7-yloxy)butan-1-ol

Yield 84.6%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONUpon completion of addition the reaction mixture
2. 2
   workup.STIRRINGwas stirred at ambient temperature during a three-hour period
3. 3
   ExtractionThe mixture was then extracted with four 50 mL portions of diethyl ether
4. 4
   WashThe combined extracts were washed with one 50 mL portion of water
5. 5
   Dryingdried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationthe filtrate was concentrated under reduced pressure

Procedure

With stirring, a solution of 2.24 grams (0.056 mole) of sodium ydroxide in 125 mL of methanol was added 8.0 grams (0.028 mole) of 4-(2,2-dimethyl-2,3-dihydrobenzo[2,3-b]furan-7-yloxy)butyl acetate. Upon completion of addition the reaction mixture was stirred at ambient temperature during a three-hour period. After this time 150 mL of water was added to the reaction mixture, and the mixture was acidified to a pH of 6 with concentrated hydrochloric acid. The mixture was then extracted with four 50 mL portions of diethyl ether. The combined extracts were washed with one 50 mL portion of water, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, yielding 5.6 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Source