Heptanoic Acid → 4-(5-Octyl-2-pyridyl)phenyl heptanoate

HRID 1491967Notes

Reaction equation

HRID 1491967 reaction equation
[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:22](O)(=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][N:13]=2)=[CH:16][CH:17]=1)(=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-

Product 1

HCID 189543534-(5-Octyl-2-pyridyl)phenyl heptanoateYield 65.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(5-Octyl-2-pyridyl)phenol (0.5 g), 0.2 g of heptanoic acid and 0.04 g 4-(dimethylamino)pyridine were dissolved in 50 ml of dichloromethane and the solution was treated portion wise with 0.4 g of N,N'-dicyclohexylcarbodiimide within 10 minutes while stirring. The mixture was stirred at room temperature overnight and then filtered. The filtrate was diluted with dichloromethane, washed twice with 50 ml of saturated sodium carbonate solution each time and then with water, dried over magnesium sulphate, filtered and subsequently concentrated. The crude product obtained was purified by chromatography on silica gel with toluene. Recrystallization from ethanol gave 0.4 g of 4-(5-octyl-2-pyridyl)phenyl heptanoate with a m.p. (C--S) 57° C. and cl.p. (S--I) 77° C.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationfiltered
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed twice with 50 ml of saturated sodium carbonate solution each time
  5. dry with materialwith water, dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationsubsequently concentrated
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel with toluene
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-81011534aecd494c977acacb607e6178
Source dataset
uspto-grants-1994_12
Patent number
US05371230

Reaction notes

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