4-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methanol → 4-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methane

HRID 1647312Notes

Reaction equation

HRID 1647312 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)O)=[CH:5][CH:4]=1>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 3681404-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methanol

Product 1

HCID 3681414-Methoxyphenyl-(3,4,5-trimethoxyphenyl)methane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 28 (304 mg, 1 mmol) in EtOAc (20 mL) was hydrogenated at 60 psi in the presence of 10% Pd-C (60 mg) for 12 h. The solution was filtered, and solvents were evaporated. The crude product was purified by crystallization from EtOAc and hexane (183 mg, 60%); mp 66°-67° C.; 1H NMR (CDCl3, 200 MHz) δ7.12 (d, J=8.5 Hz, 2H), 6.85 (d, J=8.5 Hz, 2H), 6.39 (s, 2H), 3.87 (s, 2H), 3.82 (s, 3H), 3.81 (s, 6H), 3.79 (s, 3H); CIMS (isobutane) m/e 289 (MH+, 100). Anal. (C17H20O4) C, H.

Workup

  1. filtrationThe solution was filtered
  2. customsolvents were evaporated
  3. customThe crude product was purified by crystallization from EtOAc and hexane (183 mg, 60%)

Sources & evidence

ORD record
ord-0c2fd13fefde4616be5d38264e540190
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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