3,7-Dimethyloct-6-en-1-yl carbonochloridate → HCID 22765455, compound

HRID 1111839Notes

Reaction equation

HRID 1111839 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:8])=[O:3].[C:15]([O-:18])([CH3:17])=[CH2:16].[K+]>O1CCCC1>[C:2](=[O:3])([O:18][C:15]([CH3:17])=[CH2:16])[O:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:8]

Participants

4

Reactant 2

HCID 185209753,7-Dimethyloct-6-en-1-yl carbonochloridateHCID 23680584HCID 23680584, compound

Product 1

HCID 22765455HCID 22765455, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20.78 g (0.095 mole) of citronellyl chloroformate in 150 ml of tetrahydrofuran was added under a nitrogen atmosphere with cooling and stirring an aliquot (215 ml, 0.101 mole) of the solution of potassium isopropenolate described in EXAMPLE XVIII. The reaction temperature did not rise above 10° C. during addition. After addition was complete the cooling bath was removed and the mixture was poured into 400 ml of diethyl ether, and washed successively with one 300-ml portion and three 400-ml portions of water. The ether layer was separated and dried over magnesium sulfate. Removal of solvent under reduced pressure left a red, slightly viscous residue weighing 20.83 g, which on distillation through a rotary thin-film molecular still at 75° C. skin temperature and 0.10-0.13 mm pressure yielded 12.97 g (56.8%) of citronellyl isopropenyl carbonate as a colorless liquid. The identity of the compound was confirmed by spectral data.

Workup

  1. temperaturewith cooling
  2. additionThe reaction temperature did not rise above 10° C. during addition
  3. additionAfter addition
  4. customwas removed
  5. additionthe mixture was poured into 400 ml of diethyl ether
  6. washwashed successively with one 300-ml portion and three 400-ml portions of water
  7. customThe ether layer was separated
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of solvent under reduced pressure
  10. waitleft a red, slightly viscous residue
  11. distillationon distillation through a rotary thin-film molecular still at 75° C. skin temperature and 0.10-0.13 mm pressure

Sources & evidence

ORD record
ord-8b7f71e6b3ac426299771d7553c74c91
Source dataset
uspto-grants-1978_10
Patent number
US04119106

Reaction notes

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