Reaction #2329072

Reaction equation

4-[2,3-dichloro-5-(phenylmethoxy)phenoxy}-2,2-dimethyl-2,3-dihydrobenzo[b]furan

ethanol

→

subject compound

3-[4-(2,2-dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-4,5-dichlorophenol

Conditions

Workup

1. 1
   FiltrationUpon the theoretical uptake of hydrogen gas, the reaction mixture was filtered
2. 2
   Otherto remove the catalyst
3. 3
   Concentrationthe filtrate was concentrated under reduced pressure to a residue
4. 4
   OtherThe residue was purified with column chromatography on silica gel using 100% methylene chloride
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

A mixture of 0.5 gram (0.001 mole) of 7-{4-[2,3-dichloro-5-(phenylmethoxy)phenoxy}-2,2-dimethyl-2,3-dihydrobenzo[b]furan and 0.1 gram (catalyst) of 10% palladium on carbon in 75 mL of ethanol was placed in a Parr hydrogenation bottle and hydrogenated using a Parr hydrogenation apparatus. Upon the theoretical uptake of hydrogen gas, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 100% methylene chloride, then 5% methanol in methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.17 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Source