2-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene → 4-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-yloxy)butoxy]-3,5-dichlorophenol

HRID 731970Notes

Reaction equation

HRID 731970 reaction equation
[CH3:1][C:2]1([CH3:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([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:10][C:4]=2[O:3]1>[Pd].C(O)C>[CH3:1][C:2]1([CH3:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[C:18]([Cl:32])=[CH:19][C:20]([OH:24])=[CH:21][C:22]=3[Cl:23])=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 689998862-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene

Product 1

HCID 689969554-[4-(2,2-Dimethylbenzo[d]1,3-dioxolan-5-yloxy)butoxy]-3,5-dichlorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.29 gram (0.59 millimole) of, 2-[4-(2,2-dimethylbenzo[d]1,3-dioxolan-5-oxy)butoxy]-1,3-dichloro-5-(phenylmethoxy)benzene and 0.05 gram (catalyst) of 10% palladium on carbon in 50 mL of ethanol was subjected to hydrogenation conditions using a Parr Hydrogenator, yielding 0.24 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-49569cd592e24b7497011b461132a7f9
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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