Pyridine → Carbonochloridic acid, (9Z)-9-octadecen-1-yl ester

HRID 1910411Notes

Reaction equation

HRID 1910411 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].[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>ClCCl>[Cl:20][C:21]([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:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 5284499Oleyl Alcohol

Product 1

HCID 6441661Carbonochloridic acid, (9Z)-9-octadecen-1-yl esterYield 253%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oleyl alcohol (17.58 g, 65.40 mmol), and triphosgene (6.47 g, 21.80 mmol) were dissolved in 180 ml dichloromethane, stirred and cooled on an ice bath. Anhydrous pyridine (5.17 g of, 65.40 mmol) was added dropwise into the pre-cooled solution. The reaction mixture was stirred for an additional 2 h at room temperature, and then quickly extracted with ice water. The organic layer was combined, dried over Na2SO4 and evaporated to giving crude 18.25 g (84.3% yield) of oleyl chloroformate as liquid. 1H NMR in CDCl3: δ0.88 (t, 3H, J=6.3 Hz, CH3), 1.29 (d, 22H, J=7.7 Hz, CH2), 1.73 (t, 2H, J=6.6 Hz, βCH2), 2.02 (d, 4H, J=5.4 Hz, —CH2—CH═CH—CH2—), 4.31 (t, 2H, J=6.6 Hz, αCH2), 5.35 (m, 2H, —CH═CH—).

Workup

  1. temperaturecooled on an ice bath
  2. stirringThe reaction mixture was stirred for an additional 2 h at room temperature
  3. extractionquickly extracted with ice water
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-7a9db190e129429588cf0372dd1c34de
Source dataset
uspto-grants-2013_12
Patent number
US08603999B2

Reaction notes

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