4-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol → 4-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

HRID 546811Notes

Reaction equation

HRID 546811 reaction equation
[CH2:1]([C:3]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 574330574-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 574330624-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenolYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd—C (0.1 g) was added to a solution of 4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (Example 3-(2), Enantiomer B; 725 mg, 1.92 mmol) in ethyl acetate (10 mL), and the mixture was stirred in a hydrogen atmosphere for 40 minutes. The reaction mixture was filtered and then concentrated under reduced pressure to give the title compound (720 mg, 98%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0d51a3b9d32e4c9fa82b35f4ca3282ca
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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