Pyridine → HCID 86759352, compound

HRID 2121854Notes

Reaction equation

HRID 2121854 reaction equation
[CH:1]1([CH3:12])[CH2:6][CH2:5][CH:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:3]([OH:11])[CH2:2]1.N1C=CC=CC=1.[C:19](Cl)(=[O:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl>[C:19]([OH:37])(=[O:10])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[CH:1]1([CH3:12])[CH2:6][CH2:5][CH:4]([C:7]([OH:10])([CH3:9])[CH3:8])[CH:3]([OH:11])[CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 556998p-Menthane-3,8-diolHCID 9817754Linoleoyl chloride

Product 1

HCID 86759352HCID 86759352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 250 mL one necked bottomed flask, was charged with 7.0 g (0.040 moles) of 3,8-p-menthanediol, 100 mL of anhydrous methylene chloride and 6.9 g (0.87 moles) of anhydrous pyridine. 25.5 g (0.085 moles) of Linoleoyl chloride was pre-dissolved in 25-30 mL of anhydrous methylene chloride and charged into the additional funnel. The acid chloride solution was then added dropwise to the solution at room temperature under a nitrogen blanket over a period of 30 minutes. Upon completion of the addition, the reaction was stirred for two hours before the addition funnel was replaced with a reflux condenser. The reaction was then heated to reflux for two additional hours before cooling to ambient temperature and stirring overnight.

Workup

  1. additioncharged into the additional funnel
  2. additionUpon completion of the addition
  3. customwas replaced with a reflux condenser
  4. temperatureThe reaction was then heated
  5. temperatureto reflux for two additional hours
  6. stirringstirring overnight

Sources & evidence

ORD record
ord-91e2067b407646ce963cb63589215935
Source dataset
uspto-grants-2004_02
Patent number
US06696490B2

Reaction notes

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