Dichloromethane → 1,2-Epoxydodecane

HRID 1913979Notes

Reaction equation

HRID 1913979 reaction equation
CC#N.[OH2:4].[CH2:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(Cl)Cl>CC#N>[CH2:7]([CH:6]1[CH2:5][O:4]1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 81831-DodeceneHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 178581,2-EpoxydodecaneYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under a flow of F2 (10% in N2) of 20.0 ml min−1 (3.33 mmol h−1) passed through conduit 12, MeCN:H2O (4:1, 4.95 ml) was added to conduit 16 at a rate of 9.90 ml h−1 (110.0 mmol h−1) and dodec-1-ene 24 (0.18 g, 1.07 mmol) (in a 1:1 mixture of DCM:MeCN) was added to conduit 38 at a rate of 9.90 ml h−1. All reaction fluids were collected in pot 22 containing sodium bicarbonate solution 25 (50 ml). The reaction mixture was then added to another 25 ml of sodium bicarbonate solution, washed with DCM (3×75 ml), dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield 2-decyloxirane (0.195 g, 1.06 mmol, 99%) as a yellow oil, with no further purification required.

Workup

  1. additionwas added
  2. customAll reaction fluids
  3. customwere collected in pot 22 containing sodium bicarbonate solution 25 (50 ml)
  4. additionThe reaction mixture was then added to another 25 ml of sodium bicarbonate solution
  5. washwashed with DCM (3×75 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cee0ead88abb40378cf1a7071c557740
Source dataset
uspto-grants-2013_12
Patent number
US08609873B2

Reaction notes

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