Hydrochloric Acid → HCID 24742643, compound

HRID 419775Notes

Reaction equation

HRID 419775 reaction equation
CC(C)([O-])C.[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].Cl>O1CCCC1>[CH2:17]([CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]=[CH2:8])[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 57572811HCID 57572811, compound

Product 1

HCID 24742643HCID 24742643, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 250 mL flask containing potassium tert-butoxide (13,27 g, 108,7 mmol, 4,6 eq.) under nitrogen atmosphere was added anhydrous tetrahydrofuran (100 mL) and via cannula 1-bromo-6-propylnonane (5,87 g, 23,54 mmol) in solution with anhydrous tetrahydrofuran (20 mL) was transferred at 0° C. The mixture was then stirred at room temperature for 2 h. Hydrochloric acid (230 mL, 1 M) was added slowly and the mixture was extracted with cyclohexane (300 mL+3×100 mL). The combined organic phase was washed with aqueous sodium bicarbonate (100 mL, 1 M) and dried over magnesium sulfate. The solvent was carefully evaporated under moderate vacuum (at room temperature because of the high volatility of the alkene) to give 3,3 g (84%) of 6-propylnon-1-ene as a brown liquid. 1H NMR (CDCl3, 400 MHz) d?(ppm): 5,82 (ddt, J=6,8 Hz, J=10,2 Hz, J=16,9 Hz, H); 5,00 (broad d, J=16,9 Hz, H); 4,93 (broad d, J=10,2 Hz, H); 2,02 (dt, J=6,8 Hz, J=6,8 Hz, 2H); 1,41-1,30 (m, 2H); 1,32-1,15 (m, 11H); 0,88 (t, J=7,1 Hz, 6H′). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 139,3; 114,1; 36,8; 36,1 (2C); 34,3; 33,2; 26,0; 19,8 (2C); 14,5 (2C ). MS (IE) m/z (%): 169,1 [M+] (25); 141,1 (30); 125,0 (57); 113,0 (40); 99,0 (44); 85,0 (67); 71,0 (73).

Workup

  1. customwas transferred at 0° C
  2. extractionthe mixture was extracted with cyclohexane (300 mL+3×100 mL)
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate (100 mL, 1 M)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was carefully evaporated under moderate vacuum (at room temperature because of the high volatility of the alkene)

Sources & evidence

ORD record
ord-8249fcdd35304a21a318cde7759fe480
Source dataset
uspto-grants-2012_01
Patent number
US08093398B2

Reaction notes

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