Pyridine → 3-(4-Methylphenyl)prop-2-EN-1-YL 9-cyclopropylnonanoate

HRID 918119Notes

Reaction equation

HRID 918119 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[CH:12]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24])[CH2:14][CH2:13]1.N1C=CC=CC=1.Cl.[NH+]1C=CC=CC=1>CCOCC.O>[CH:12]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:9][CH2:8][CH:7]=[CH:6][C:5]2[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:24])[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 3611722-Propen-1-ol, 3-(4-methylphenyl)-, (2E)-HCID 214896439-Cyclopropylnonanoyl chlorideHCID 21584435Pyridinium hydrochloride

Product 1

HCID 541641133-(4-Methylphenyl)prop-2-EN-1-YL 9-cyclopropylnonanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.5 g. p-methylcinnamyl alcohol in 50 ml. ether at 0° under nitrogen is added 4.9 g. 9-cyclopropylnonanoyl chloride and 3.6 ml. pyridine. The reaction mixture is allowed to warm to room temperature and is then stirred for ten days. Water is then added to dissolve the pyridinium hydrochloride and form a second liquid phase. This mixture is stirred for 4 hours to hydrolyze the excess acid chloride and the mixture is then diluted with a mixture of ether and water. The ether phase is separated and the aqueous phase is extracated once with ether. The combined ether phases are washed with 2N sulfuric acid, 10% potassium carbonate, water, saturated copper sulfate, water, and brine, dried over calcium sulfate and the solvent removed to yield p-methylcinnamyl 9-cyclopropylnonanoate.

Workup

  1. customform a second liquid phase
  2. stirringThis mixture is stirred for 4 hours
  3. customThe ether phase is separated
  4. washThe combined ether phases are washed with 2N sulfuric acid, 10% potassium carbonate, water, saturated copper sulfate, water, and brine
  5. dry with materialdried over calcium sulfate
  6. customthe solvent removed

Sources & evidence

ORD record
ord-10ead71c796c4e88898fed505ca74c90
Source dataset
uspto-grants-1976_07
Patent number
US03969384

Reaction notes

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