Hexane → HCID 86762216, compound

HRID 469140Notes

Reaction equation

HRID 469140 reaction equation
[CH3:1][CH:2]([CH2:15][CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(N(CC)CC)C.[C:24](Cl)(=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].CCCCCC>CN(C)C1C=CN=CC=1.C(OCC)C.C(OCC)(=O)C>[C:24]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:15][CH3:16])(=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

8

Reactant 4

HCID 8058HexaneHCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 1353040312-Methyltetradecan-1-ol

Product 1

HCID 86762216HCID 86762216, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A dry 500 ml 3-neck round bottom flask fitted with a condenser is charged with 12-methyltetradecan-1-ol (10.0 g, 0.0438 mol) from example I.A, 125 ml diethyl ether, triethylamine (4.87 g, 0.0481 mol), and 4-(dimethylamino)pyridine (DMAP) 0.5350 g, 0.0044 mol). The solution is stirred at room temperature under a positive N2 atmosphere. Palmitoyl chloride (13.20 g, 0.0481 mol) in 13 ml diethyl ether is added dropwise to the reaction flask from an addition funnel at room temperature. A thick white precipitate forms. An additional 115 ml of diethyl ether is added to help stirring the thick slurry. The mixture is stirred overnight at room temperature under a nitrogen atmosphere. After 18 hours reaction time an aliquot of the mixture is spotted on a TLC plate (95:5 v/v hexane:ethyl acetate) versus the starting materials, indicating the reaction to be complete. The reaction mixture is vacuum filtered, and the filter cake rinsed with 2×400 ml diethyl ether. The filtrate is back extracted with 2×400 ml water. The ether phase is dried with anhydrous magnesium sulfate, vacuum filtered and the filtrate concentrated in vacuo on a rotary evaporator at 40° and the crude product recovered (20.3 g). The crude product is dissolved in warm ethanol (150 ml) and placed into a freezer to recrystallize the product. The precipitated product is vacuum filtered and the filter cake rinsed with 0° C. ethanol (3×50 ml). The cake is further dried in vacuo at room temperature to yield 12-methyltetradecyl palmitate as a white powdery solid (17.3 g). Yield 84.1%.

Workup

  1. customA dry 500 ml 3-neck round bottom flask fitted with a condenser
  2. stirringto help stirring the thick slurry
  3. stirringThe mixture is stirred overnight at room temperature under a nitrogen atmosphere
  4. customAfter 18 hours reaction time an aliquot of the mixture
  5. customthe reaction
  6. filtrationfiltered
  7. washthe filter cake rinsed with 2×400 ml diethyl ether
  8. extractionThe filtrate is back extracted with 2×400 ml water
  9. dry with materialThe ether phase is dried with anhydrous magnesium sulfate, vacuum
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo on a rotary evaporator at 40°
  12. customthe crude product recovered (20.3 g)
  13. dissolutionThe crude product is dissolved in warm ethanol (150 ml)
  14. customto recrystallize the product
  15. filtrationfiltered
  16. washthe filter cake rinsed with 0° C. ethanol (3×50 ml)
  17. customThe cake is further dried in vacuo at room temperature

Sources & evidence

ORD record
ord-51ff0d68aeed48e69c5fc21fed8a9667
Source dataset
uspto-grants-2014_01
Patent number
US08628760B2

Reaction notes

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