Hydrochloric Acid → (Z,Z,E)-7,11,13-Hexadecatrienal

HRID 74325Notes

Reaction equation

HRID 74325 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH:16]=[CH:17]\[CH2:18][CH3:19])C.Cl>C1(C)C=CC=CC=1>[CH:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH:16]=[CH:17]\[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86762707(Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene

Product 1

HCID 25067736(Z,Z,E)-7,11,13-HexadecatrienalYield 82.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
22.5 °C

Procedure

(Z,Z,E)-1,1-Diethoxy-7,11,13-hexadecatriene (49.36 g, 0.16 mol) and toluene (30 g) were placed in a reaction vessel and stirred at 20 to 25° C. for 30 minutes. After stirring, 10% by weight hydrochloric acid (19.3 g) was added dropwise to the reaction mixture at 20 to 25° C., and stirred for one hour. The reaction mixture was separated into phases. Then, the organic phase was washed with an aqueous sodium bicarbonate solution, and concentrated by removal of the solvent under reduced pressure to obtain (Z,Z,E)-7,11,13-hexadecatrienal (30.47 g, 0.13 mol) with a yield of 82.7%.

Workup

  1. stirringAfter stirring
  2. stirringstirred for one hour
  3. customThe reaction mixture was separated into phases
  4. washThen, the organic phase was washed with an aqueous sodium bicarbonate solution
  5. concentrationconcentrated by removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f4b1d4712982406b8d61953f83180678
Source dataset
uspto-grants-2014_09
Patent number
US08829255B1

Reaction notes

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