1-Ethynylcyclohexanol → 1-Ethynylcyclohexyl methyl carbonate

HRID 258588

Reaction equation

HRID 258588 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[Na].Cl[C:12]([O:14][CH3:15])=[O:13]>C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:12](=[O:13])([O:9][C:3]1([C:1]#[CH:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[O:14][CH3:15]

Participants

6

Reactant 3

HCID 65251-EthynylcyclohexanolHCID 6586Methyl chloroformateHCID 5360545Sodium2×

Product 1

HCID 135708701-Ethynylcyclohexyl methyl carbonate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 36.0 gm of 1-ethynylcyclohexanol in 50 ml of benzene was slowly added drop-by-drop to an agitated suspension, cooled to 0° to 5° C., of 5.5 gm of finely distributed sodium in 50 ml of absolute toluene and 250 ml of benzene, and was agitated at room temperature until reaction had been completed. 26.0 gm of methyl chloroformate were added under cooling to the sodium salt which has been formed. The mixture was allowed to react for 12 hours at room temperature and was washed several times with water and dried. After distilling off the solvent, the raw ester was fractionated by means of a 20 cm Vigreux column. The methyl 1-ethynylcyclohexyl carbonate thus obtained constitutes a coloroless liquid having a fruity, herbal, complex odor and a distinctive fragrance of dill, and has the following characteristic values:

Workup

  1. customhas been formed
  2. customto react for 12 hours at room temperature
  3. washwas washed several times with water
  4. customdried
  5. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-2d4152fd3d184abaa38cef06fb156029
Source dataset
uspto-grants-1977_07
Patent number
US04033993

Linked notes

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