Hexanal → HCID 12960857, compound

HRID 1389069Notes

Reaction equation

HRID 1389069 reaction equation
[OH-].[Na+].[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])C=CC=CC=1.[CH:38](=O)[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CS(C)=O>[C:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:38]\[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6184HexanalHCID 14798Sodium HydroxideHCID 20298006HCID 20298006, compound

Product 1

HCID 12960857HCID 12960857, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
70 °C

Procedure

30 ml. of dry dimethyl sulfoxide are poured into a 200 ml. of four-necked flask equipped with a stirrer, a dropping funnel, a gas inlet tube, a thermometer and a condenser. 2.5 g. (0.13 moles) of sodium hydroxide (80% oily suspension) are introduced into the flask, and the mixture is stirred at 70° C. under argon temperature until the gas evolution ceases (0.5 hours). The reaction mixture is cooled to room temperature, a solution of 20 g. (0.036 moles) of triphenyl-(11-acetoxy-undecyl)-phosphonium bromide (Formula V, X=Br, Y=COCH3) in 20 ml. of dry dimethyl sulfoxide is added, and the resulting mixture is stirred at room temperature for 0.5 hours. There are added dropwise to the red solution 4 g. (0.04 moles) of hexanel (Formula IV, R=CH3), and the mixture is stirred at room temperature for 15 hours. The reaction mixture is poured onto 60 g. of ice, and extracted with 200 ml. of hexane. The extract is washed successively with water, 10% aqueous sulfuric acid, water, saturated aqueous sodium bicarbonate solution and again with water, dried over magnesium sulfate, filtered, and the solvent is evaporated in vacuo. 2.34 g. (22%) of (Z)-11-heptadecenyl acetate (Formula I, R=CH3) are obtained; b.p.: 122°-125° C./0.05 mmHg.

Workup

  1. customof four-necked flask equipped with a stirrer, a dropping funnel, a gas inlet tube
  2. temperatureThe reaction mixture is cooled to room temperature
  3. stirringthe resulting mixture is stirred at room temperature for 0.5 hours
  4. additionThe reaction mixture is poured onto 60 g
  5. extractionof ice, and extracted with 200 ml
  6. washThe extract is washed successively with water, 10% aqueous sulfuric acid, water, saturated aqueous sodium bicarbonate solution and again with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-7822878944ed4cd79af6fab1c0887ba1
Source dataset
uspto-grants-1981_01
Patent number
US04243660

Reaction notes

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