Hydrochloric Acid → 2-Tridecene, (2Z)-

HRID 982558Notes

Reaction equation

HRID 982558 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-].[CH3:15][Al](C)C.[Na+].C[O-].[Na+].Cl>CCCCC>[CH3:13]/[CH:12]=[CH:11]\[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 200682281-Chloro-1-dodecyneHCID 23710214Sodium trimethylaluminum hydride

Product 1

HCID 53627142-Tridecene, (2Z)-

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
50 °C

Procedure

By a procedure similar to that described in Example 9, 1.00 g (5.00 mmol) of 1-chloro-1-dodecyne was hydroaluminated with sodium trimethylaluminum 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 2% 1-dodecene, 29% 1-dodecyne, and 69% cis-2-tridecene. Short-path distillation provided a pure sample of cis-2-tridecene; bp=49./0.2 torr; IR (neat) 3050 (w), 2960 (m), 2920 (s), 2850 (s), 1660 (w), 1470 (m) cm-1 ; 1H--NMR (CDCl 3, TMS) (ppm) 0.85 (t, 3H), 1.2 -1.4 (br s, 16H), 1.55 (d, J= 6 Hz, 3H), 2.0 (m, 2H), 5.40 (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-1b45cb7ccf9a4c75a12b1af6485e2af3
Source dataset
uspto-grants-1991_02
Patent number
US04996340

Reaction notes

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