Ethanol → 2-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-4-hydroxy-8-n-propylchroman

HRID 1285256Notes

Reaction equation

HRID 1285256 reaction equation
[C:1]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([OH:33])[C:25]=1[CH2:34][CH2:35][CH3:36])[C:9]=2[CH2:37][CH2:38][CH3:39])([O:3][CH2:4][CH3:5])=[O:2].C(O)C>O1CCCC1.[Ni]>[C:1]([CH:6]1[CH2:15][CH:14]([OH:16])[C:13]2[C:8](=[C:9]([CH2:37][CH2:38][CH3:39])[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([OH:33])[C:25]=3[CH2:34][CH2:35][CH3:36])=[CH:11][CH:12]=2)[O:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 135378612-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromone

Product 1

HCID 135378792-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-4-hydroxy-8-n-propylchromanYield 50%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 2, 14.3 g (0.027 mole), was dissolved in 150 ml tetrahydrofuran and 150 ml ethyl alcohol and hydrogenated using Raney Nickel (4.2 g) at 2 psi. After 24 hours at room temperature, the catalyst was separated by filtration and the solvent stripped to give crude (14.4 g oil). 2.4 of the crude was chromatographed (50% ethyl acetate-hexane) to give 1.4 g (50% yield based on crude taken) of the title compound as an oil. Calc: C, 68.61; H, 7.80. Found: C, 68.34; H, 7.74.

Workup

  1. customthe catalyst was separated by filtration

Sources & evidence

ORD record
ord-9493beaa0d634ec29031170638779db3
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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