Pyridine → Cyclooctyl methyl carbonate

HRID 1679254

Reaction equation

HRID 1679254 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH:6]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.N1C=CC=CC=1.Cl.N1C=CC=CC=1>C1C=CC=CC=1>[C:2](=[O:3])([O:14][CH:6]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[O:4][CH3:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6586Methyl chloroformate2×HCID 12766CyclooctanolHCID 10176127Pyridinium chloride

Product 1

HCID 109116Cyclooctyl methyl carbonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

18.9 gm of methyl chloroformate were added drop-by-drop under agitation to a solution of 25.6 gm of cyclooctanol and 15.8 gm of absolute pyridine in 150 ml of dry benzene under external cooling at 0° to 5° C. After the methyl chloroformate had been added, agitation was continued for 12 hours at room temperature. Then, the benzene phase was drawn off from the precipitated pyridine hydrochloride, and washed with diluted hydrochloric acid, sodium hydroxide solution and water, and dried. After the solvent had been distilled off, the raw ester was distilled in vacuo by means of a Vigreux column. A colorless liquid was obtained which had a herbal, very natural and complex fragrance which is distinguished by a strong and long-clinging flowery jasmine scent.

Workup

  1. temperatureunder external cooling at 0° to 5° C
  2. washwashed with diluted hydrochloric acid, sodium hydroxide solution and water
  3. customdried
  4. distillationAfter the solvent had been distilled off
  5. distillationthe raw ester was distilled in vacuo by means of a Vigreux column
  6. customA colorless liquid was obtained which

Sources & evidence

ORD record
ord-5e0547f65903437287645273aa359a18
Source dataset
uspto-grants-1978_03
Patent number
US04080309

Linked notes

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