Water → HCID 117640724, compound

HRID 1773121Notes

Reaction equation

HRID 1773121 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH:14](OCC)[O:15]CC.O>C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][CH:14]=[O:15]

Participants

5

Reactant 2

HCID 962WaterHCID 117640727HCID 117640727, compound

Product 1

HCID 117640724HCID 117640724, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62.5 °C

Procedure

In a reactor equipped with a stirrer, a cooling condenser, a dropping funnel and a thermometer were placed 13-chloro-1,1-diethoxy-2-tridecyne (302.9 g:1.0 mol), para-toluenesulfonic acid (8.0 g:0.05 mol), water (170.0 g) and tetrahydrofuran (42.0 g), and then stirred at a reaction mixture temperature of from 60 to 65° C. During stirring, the pressure in the reactor was reduced gradually to 26.7 KPa to distill off refluxing ethanol. After stirring for 5 hours, completion of the reaction was confirmed by gas chromatography. The organic phase separated from the aqueous phase of the reaction mixture was washed with a solution of sodium chloride (5.0 g) in water (150.0 g). The organic phase was subjected to removal of the solvent under reduced pressure, and then the residue was distilled under reduced pressure to obtain 13-chloro-2-tridecynal [bp: 116-122° C./0.13 KPa, 198.6 g, 0.87 mol]. [Yield: 86.8%]

Workup

  1. customIn a reactor equipped with a stirrer, a cooling condenser, a dropping funnel
  2. stirringDuring stirring
  3. distillationto distill off
  4. temperaturerefluxing ethanol
  5. stirringAfter stirring for 5 hours
  6. customThe organic phase separated from the aqueous phase of the reaction mixture
  7. washwas washed with a solution of sodium chloride (5.0 g) in water (150.0 g)
  8. customThe organic phase was subjected to removal of the solvent under reduced pressure
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-6417da721b8a44a7ada15afce7be2042
Source dataset
uspto-grants-2016_02
Patent number
US09255056B2

Reaction notes

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