Ammonium Chloride → HCID 6538161, compound

HRID 2086520Notes

Reaction equation

HRID 2086520 reaction equation
COC([CH2:5][CH:6](C1CO1)[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=O.C([Mg]Cl)C=C.C(Cl)/C=C(/CCC=C(C)C)\C.[NH4+].[Cl-]>CCOCC.C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:17]/[C:10](/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:9]\[CH2:8][CH2:7][CH:6]=[CH2:5]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6372219Geranyl chlorideHCID 86759427HCID 86759427, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 6538161HCID 6538161, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 86583969tetrahydrofuran HMPASolvent

Procedure

For the synthesis of the (E)-6,10-dimethyl-2-oxiranylundeca-5,9-dienecarboxylic acid methyl ester, 27.00 ml (54.00 mmol) of a 2 M solution of allylmagnesium chloride in ether is added dropwise within 30 minutes to a solution of 1.10 g (6.40 mmol) of geranyl chloride in 50 ml of THF/HMPT (v/v=1/1). The resulting mixture is stirred at room temperature for 15 hours, and then 20 ml of saturated aqueous NH4Cl solution is added. The organic phase is separated off, and the aqueous phase is extracted four times with 25 ml each of dichloromethane. The combined organic phases are concentrated under reduced pressure. The remaining residue is taken up with 50 ml of ether, successively washed with 2 M aqueous hydrochloric acid, saturated aqueous NaCl solution and distilled water, dried over MgSO4 and concentrated under reduced pressure. The vacuum distillation of the thus obtained residue yields 0.89 g (4.99 mmol, 78%) of (E)-6,10-dimethyl-undeca-1,5,9-triene.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted four times with 25 ml each of dichloromethane
  3. concentrationThe combined organic phases are concentrated under reduced pressure
  4. washsuccessively washed with 2 M aqueous hydrochloric acid, saturated aqueous NaCl solution
  5. distillationdistilled water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. distillationThe vacuum distillation of the thus obtained residue

Sources & evidence

ORD record
ord-2c5646e9663d489d8ec8ade3a6ff4d64
Source dataset
uspto-grants-2004_04
Patent number
US06726911B1

Reaction notes

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