Acetylene → HCID 131711350, compound

HRID 1704699Notes

Reaction equation

HRID 1704699 reaction equation
[CH:1]#C.Cl[CH2:4][Cl:5].[Cl-].[Al+3].[Cl-].[Cl-].[O:10]=[C:11]([CH3:18])[CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>C(Cl)(Cl)(Cl)Cl>[Cl:5]/[CH:4]=[CH:1]/[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11](=[O:10])[CH3:18]

Participants

6

Reactant 4

HCID 6326Acetylene3×HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 13839457HCID 13839457, compound

Product 1

HCID 131711350HCID 131711350, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

Acetylene was passed through 69 ml of carbon tetrachloride contained in a 250 ml three-necked, round-bottomed flask equipped with a gas inlet tube, mechanical stirring, addition funnel and reflux condenser for 5 minutes. Alternately, dichloromethane can also be used as a solvent. The solvent was cooled to 0° C., 7.19 g of aluminum chloride added and acetylene passed through the slurry for an additional 5 minutes. A solution of 5.70 g of 5-ketohexanoylchloride in 6.5 ml of carbon tetrachloride was added dropwise. Acetylene was passed through the stirred mixture for an additional 4.5 hours. The reaction mixture was poured onto an ice-brine mixture, the layers separated and the aqueous layer extracted twice with ether. The combined organic layers were washed with 10% hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried over MgSO4, filtered and evaporated in vacuo, to yield 2.10 g of a brown oil. This material was bulb-to-bulb distilled (vacuum pump) to yield 1.57 g of a light yellow oil. This material was combined with 1.2 g of crude product from a similar reaction sequence and purified by column chromatography (Silica Gel, 2.5% acetone in dichloromethane) to yield 585 mg of the diketooctene as a yellow oil. The material had the following spectral characteristics: nmr δ 2.15 (s, 3, COCH3), 2.52 (complex, 4, CH2CO), 2.00 (complex, CH2CH2CH2), 6.50 (d, 1, =CHCl), 7.42 (d, J=14Hz, =CHCO); ir λ max 5.85, 6.30, 7.35, 10.70μ.

Workup

  1. customround-bottomed flask equipped with a gas inlet tube
  2. additionmechanical stirring, addition funnel
  3. temperaturereflux condenser for 5 minutes
  4. customthe layers separated
  5. extractionthe aqueous layer extracted twice with ether
  6. washThe combined organic layers were washed with 10% hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d274c04e8df04b02842aa01a0edc9896
Source dataset
uspto-grants-1978_11
Patent number
US04127612

Reaction notes

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