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

HRID 1285247Notes

Reaction equation

HRID 1285247 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:12]([C:13](=O)[CH:14]=1)=[CH:11][CH:10]=[C:9]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=1[CH2:33][CH2:34][CH3:35])[C:8]=2[CH2:36][CH2:37][CH3:38])([O:3][CH3:4])=[O:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:36][CH2:37][CH3:38])[C:9]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=2)[O:6]1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 135378622-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromoneHCID 178418361HCID 178418361, compound

Product 1

HCID 135378702-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromanYield 89.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

7.65 g (14.6 mmole) of the compound from Example 5 was hydrogenated in 80 ml of acetic acid at 70° C. and 50 psi pressure in a 250 ml Parr shaker using 5% palladium on carbon as the catalyst. Theoretical hydrogen uptake occurred at 40 minutes. The shaker was cooled and vented, and its contents filtered. The filtrate was placed in a rotary evaporator and the acetic acid was removed by azeotropation three times with toluene and then once with methyl alcohol. Recrystallization from ethyl acetatehexane yielded 6.7 g (89%) of the title compound, mp 57°-58°, Calc: C, 70.29; H, 7.86; Found C, 70.09; H, 7.76.

Workup

  1. temperatureThe shaker was cooled
  2. filtrationits contents filtered
  3. customThe filtrate was placed in a rotary evaporator
  4. customthe acetic acid was removed by azeotropation three times with toluene
  5. customRecrystallization from ethyl acetatehexane

Sources & evidence

ORD record
ord-9af9da71db7a438cb5a74f02c7f5e06c
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

Loading…