Pyridine → HCID 70179053, compound

HRID 2187350Notes

Reaction equation

HRID 2187350 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C@H:8]1[CH2:12][CH2:11][C@@:10]([CH3:14])([OH:13])[C@H:9]1[CH3:15])([CH3:7])=[CH2:6].C(OC(=O)C)(=O)C.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:13][C@:10]1([CH3:14])[CH2:11][CH2:12][C@H:8]([C:5]([CH3:7])=[CH2:6])[C@@H:9]1[CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 15602234cyclopentanol, 1,2-dimethyl-3-(1-methylethenyl)-, [1r-(1alpha,2alpha,3alpha)]-

Product 1

HCID 70179053HCID 70179053, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

Acetyl chloride (27 g; 0.34 mol) was added dropwise to a stirred solution of (1R,2S,3S)-3-isopropenyl-1,2-dimethyl-1-cyclopentanol (50 g; 0.32 mol), acetic anhydride (20 g; 0.2 mol), pyridine (57 g; 0.72 mol) and toluene (600 ml) at room temperature and heated to 45° C. during 3 days. The cooled reaction mixture was poured onto ice and washed with H2SO4 (10%), water, NaHCO3 solution (5%) and brine, then distilled at 53-56°/0.7 hPa to give 59 g of (1R,2S,3S)-3-isopropenyl-1,2-dimethyl-1-cyclopentyl acetate of 90% purity. Fractional distillation finished 93% pure (1R,2S,3S)-3-isopropenyl-1,2-dimethyl-1-cyclopentyl acetate (48.7 g; 76.6%). This product showed an odor of the lactonic type, with connotations of jasmine and terpenyl acetate.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured onto ice
  3. washwashed with H2SO4 (10%), water, NaHCO3 solution (5%) and brine
  4. distillationdistilled at 53-56°/0.7 hPa

Sources & evidence

ORD record
ord-74f55055d8d74141b248c7f7a8c2fb19
Source dataset
uspto-grants-2002_06
Patent number
US06410504B1

Reaction notes

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