Hydrochloric Acid → Octadecanoic acid, 3-oxo-, ethyl ester

HRID 974691Notes

Reaction equation

HRID 974691 reaction equation
C([Li])CCC.C1(NC(C)C)CCCCC1.[C:16](Cl)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].Cl.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36]>CCCCCC.O1CCCC1.C(OCC)C>[O:32]=[C:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:36][C:35]([O:38][CH2:39][CH3:40])=[O:37]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8206Palmitoyl chlorideHCID 8857Ethyl AcetateHCID 62386CyclohexylisopropylamineHCID 178418339Butyllithium

Product 1

HCID 112885Octadecanoic acid, 3-oxo-, ethyl ester

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

502 ml of a 15.12% by weight solution of butyllithium in hexane was added dropwise at -78° C. over a period of 30 minutes to a solution of 128 ml of cyclohexylisopropylamine in 800 ml of tetrahydrofuran. After the addition was complete, the reaction mixture was allowed to warm up to 0° C. over a period of 30 minutes. It was then again cooled to -78° C., after which 38 ml of ethyl acetate were added over a period of 5 minutes. The mixture was then stirred at the same temperature for 10 minutes, after which 75.0 g of palmitoyl chloride were added dropwise to it over a period of 5 minutes. The mixture was then stirred at -78° C. for 10 minutes, after which 250 ml of 20% v/v aqueous hydrochloric acid was added dropwise to the reaction mixture. The reaction mixture was then allowed to warm to room temperature, and 1 liter of diethyl ether was added. The resulting two layers were separated, and the aqueous layer was extracted with diethyl ether. The organic layer was combined with the extract, and this was washed, in turn, with a saturated aqueous solution of sodium bicarbonate and with an aqueous solution of sodium chloride. It was then dried and concentrated by evaporation under reduced pressure. The residue was allowed to stand to produce crystals, which were collected by filtration, to give 55.61 g of the title compound. Recrystallization of the product from cold ethanol gave white prisms melting at 38°-39° C.

Workup

  1. additionAfter the addition
  2. temperatureIt was then again cooled to -78° C.
  3. stirringThe mixture was then stirred at -78° C. for 10 minutes
  4. temperatureto warm to room temperature
  5. customThe resulting two layers were separated
  6. extractionthe aqueous layer was extracted with diethyl ether
  7. washthis was washed, in turn, with a saturated aqueous solution of sodium bicarbonate and with an aqueous solution of sodium chloride
  8. customIt was then dried
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customto produce crystals, which
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d084a888f9f64c00acf68d5b96ef6ab1
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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