Pyridine → HCID 86739071, compound

HRID 647761Notes

Reaction equation

HRID 647761 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29]>CCOCC>[C:26]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 5284499Oleyl Alcohol

Product 1

HCID 86739071HCID 86739071, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Oleyl alcohol (40 g, Eastman) and anhydrous pyridine (10 ml) were added to a 100 ml round-bottom flask equipped with a magnetic stirrer. The mixture was stirred and cooled in an ice bath for five minutes. Butyryl chloride (15.0 g, 0.14 mol, Eastman) was added dropwise via an addition funnel. The reaction mixture was stirred for 15 minutes at 5° and at room temperature for an hour. It was then diluted with ether and filtered. The filtrate was dried over sodium sulfate. Volatiles were removed under vacuum. Distillation of the residual oil (163°-168°, 0.26-0.28 torr) gave 16.2 g (34%) of 3. NMR: δ 0.9 (m, 6 H, CH3), 1.1-2.4 (m, 32 H, CH2), 3.95 (t, J=6 Hz, CH2O), 5.3 (t, J=4.5 Hz, 2 H vinyl). IR: 3005 (olefinic-CH), 1740 (C=O), 1175 cm-1 (C--O--C)

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturecooled in an ice bath for five minutes
  3. stirringThe reaction mixture was stirred for 15 minutes at 5° and at room temperature for an hour
  4. filtrationfiltered
  5. dry with materialThe filtrate was dried over sodium sulfate
  6. customVolatiles were removed under vacuum
  7. distillationDistillation of the residual oil (163°-168°, 0.26-0.28 torr)

Sources & evidence

ORD record
ord-3b10452bd154481dbfd2dcb06fa95920
Source dataset
uspto-grants-1983_10
Patent number
US04410509

Reaction notes

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