HCID 66968111, compound → 4-(2-Phenyl-tetrahydro-pyran-2-yl)-phenol

HRID 70736Notes

Reaction equation

HRID 70736 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:20][CH:19]=[CH:18][CH2:17][O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:21]1([C:15]2([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 1

HCID 66968111HCID 66968111, compound

Product 1

HCID 167347324-(2-Phenyl-tetrahydro-pyran-2-yl)-phenolYield 101.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Benzyloxy-phenyl)-2-phenyl-3,6-dihydro-2H-pyran (4.1 g) was dissolved in methanol (25 mL) and ethyl acetate (5 mL). 5% Palladium on carbon (10 mg) was added. Nitrogen was bubbled through the solution. Ammonium acetate (4 g) was added. The mixture was stirred for 6 h, filtered through a block of celite and concentrated to a solid. NMR indicated full conversion to the title product (3.1 g, 12.2 mmol).

Workup

  1. customNitrogen was bubbled through the solution
  2. additionAmmonium acetate (4 g) was added
  3. filtrationfiltered through a block of celite
  4. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-1d96e7c079b547f99ccac73908bb7b80
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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