Hydrochloric Acid → 3-Tetradecene, (3Z)-

HRID 982559Notes

Reaction equation

HRID 982559 reaction equation
Cl[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[H-].[CH2:15]([Al](CC)CC)[CH3:16].[Na+].C[O-].[Na+].Cl>CCCCC>[CH3:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 200682281-Chloro-1-dodecyneHCID 23710215Sodium triethylaluminum hydride

Product 1

HCID 53627093-Tetradecene, (3Z)-

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
50 °C

Procedure

In a manner similar to that described in Example 10, 1.00 g (5.00 mmol) of 1-Chloro-1-dodecyne was hydroaluminated with sodium triethylaluminum hydride and then treated with sodium methoxide. After heating the reaction mixture overnight at 50° C., it was slowly poured into a mixture of 3N HCl and pentane. The aqueous layer was extracted with pentane and the combined organic phase was washed sequentially with 3N HCl, saturated NaHCO3, and saturated NaCl. Analysis by GC (using n-nonane as an internal standard) showed the presence of 4% 1-dodecene, 28% 1-dodecyne, and 68% cis-3-tetradecene. Short-path distillation provided a pure sample of cis-3-tetradecene: bp=57./0.1 torr; IR (neat) 3020 (w), 2960 (s), 2920 (s), 2850 (s), 1655 (w), 1470 (m) cm-1 ; 1H--NMR (CDC13, TMS) 0.85 (t, 3H), 0.95 (t, 3H), 1.2-1.4 (br s, 16H), 2.05 (m, 4H), 5.35 (m, 2H).

Workup

  1. extractionThe aqueous layer was extracted with pentane
  2. washthe combined organic phase was washed sequentially with 3N HCl, saturated NaHCO3, and saturated NaCl
  3. distillationShort-path distillation

Sources & evidence

ORD record
ord-c5e77dbda7c14c9aa5df25a21024930d
Source dataset
uspto-grants-1991_02
Patent number
US04996340

Reaction notes

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