Pyridine → HCID 70179053, compound

HRID 568198Notes

Reaction equation

HRID 568198 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 furnished 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-fa1083a579af48fda5944f9e3f71bb11
Source dataset
uspto-grants-2001_01
Patent number
US06180814B2

Reaction notes

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