2-(Benzyloxy)-3-tert-butyl-3'-(1-(2-methoxyphenyl)vinyl)biphenyl → 3-tert-Butyl-3'-(1-(2-methoxyphenyl)ethyl)biphenyl-2-ol

HRID 45476Notes

Reaction equation

HRID 45476 reaction equation
C([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[CH2:26])[CH:20]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[CH3:26])[CH:20]=2)[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 1

HCID 582385762-(Benzyloxy)-3-tert-butyl-3'-(1-(2-methoxyphenyl)vinyl)biphenyl

Product 1

HCID 582385893-tert-Butyl-3'-(1-(2-methoxyphenyl)ethyl)biphenyl-2-olYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 38 (0.7 g, 1.56 mmol) in methanol (40 mL) and ethyl acetate (60 mL) was treated with 20% palladium on activated carbon (50% wet, 0.100 g) and was hydrogenated at 40 psi in a Parr shaker for 4 hr. The catalyst was filtered out and washed with ethyl acetate. The filtrate was stripped and the crude product was purified by chromatography on silica (40 g) hexane (3 L) to afford pure E2 (0.54 g, 96%).

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with ethyl acetate
  3. customthe crude product was purified by chromatography on silica (40 g) hexane (3 L)

Sources & evidence

ORD record
ord-b4df023692c240fda132f3cba874f8c0
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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