HCID 86603464, compound → HCID 86603465, compound

HRID 1171015Notes

Reaction equation

HRID 1171015 reaction equation
[CH3:1][C:2]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[C:13]([CH:21]([CH3:23])[CH3:22])[CH:12]=2)=[C:8]([CH3:24])[CH:7]=[C:6]([OH:25])[C:3]=1[CH2:4]O>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH3:20][O:19][CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]2[C:8]([CH3:24])=[CH:7][C:6]([OH:25])=[C:3]([CH3:4])[C:2]=2[CH3:1])=[CH:12][C:13]=1[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 1

HCID 86603464HCID 86603464, compound

Product 1

HCID 86603465HCID 86603465, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

A mixture of 2,4-dimethyl-6-hydroxy-3-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzyl alcohol ((0.20 g, 0.58 mmol) and Pd—C (0.08 g, 10%) in ethyl acetate-acetic acid (3.5 mL, 95:5) was stirred at room temperature under a H2 atmosphere for 6 h. The reaction mixture was filtered through a Celite plug and the solvent was removed under reduced pressure to afford 4-(4′-methoxymethoxy-3′-iso-propylbenzyl)-2,3,5-trimethylphenol (0.19 g, 100%) as colorless oil: 1H NMR (300 MHz, CD3OD): δ 6.94 (m, 1 H), 6.91 (d, J=13.2 Hz, 1 H), 6.68 (dd, J=13.2, 2.4 Hz, 1 H), 6.55 (s, 1 H), 5.17 (s, 2 H), 3.95 (s, 2 H), 3.47 (s, 3 H), 3.30 (m, 1 H), 2.19 (s, 3 H), 2.16 (s, 3 H), 2.11 (s, 3 H), 1.17 (d, J=10.8 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=acetone-hexanes (3:7); Rf=0.60.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite plug
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a2d2aa46d6614900a61dde2cf1dc9907
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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