2-[4-(2,2-Dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene → 4-[4-(2,2-Dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-3,5-dichlorophenol

HRID 1611452Notes

Reaction equation

HRID 1611452 reaction equation
[CH3:1][C:2]1([CH3:33])[O:6][C:5]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([O:24]CC4C=CC=CC=4)=[CH:19][C:18]=3[Cl:32])=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:33])[O:6][C:5]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([OH:24])=[CH:19][C:18]=3[Cl:32])=[CH:8][CH:9]=[CH:10][C:4]=2[CH2:3]1

Participants

4

Reactant 1

HCID 222571322-[4-(2,2-Dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene

Product 1

HCID 222571444-[4-(2,2-Dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-3,5-dichlorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.67 gram (0.0014 mole) of, 2-[4-(2,2-dimethyl(2,3-dihydrobenzo[2,3-b]furan-7-yloxy))butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene and 0.01 gram (catalyst) of 10% palladium on carbon in 75 mL of methanol was subjected to hydrogenation conditions using a Parr Hydrogenator, yielding 0.55 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-b44dbd208efb4d4a91071fb46071ac8d
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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