Water → 4-n-Pentylcyclohexylmethyl methanesulfonate

HRID 342322Notes

Reaction equation

HRID 342322 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:14][S:15]([O:13][CH2:12][CH:9]1[CH2:8][CH2:7][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]1)(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 13548135(4-Pentylcyclohexyl)methanol

Product 1

HCID 541366984-n-Pentylcyclohexylmethyl methanesulfonateYield 99.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

8.0 g of 4-n-pentylcyclohexylmethanol was dissolved in a mixture solvent of 8 ml of pyridine and 8 ml of toluene. To the solution, 6.0 g of methanesulfonyl chloride was added dropwise below 10° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was poured into cold water and subjected to extraction with toluene, followed by washing successively with 5%-hydrochloric acid aqueous solution and water and drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 11.3 g of 4-n-pentylcyclohexylmethyl methanesulfonate.

Workup

  1. customAfter the reaction
  2. extractionsubjected to extraction with toluene
  3. washby washing successively with 5%-hydrochloric acid aqueous solution and water
  4. dry with materialdrying with anhydrous magnesium sulfate
  5. filtrationThe resultant organic layer was subjected to filtration

Sources & evidence

ORD record
ord-ca8534a1906f46efa1363e478d827682
Source dataset
uspto-grants-1999_01
Patent number
US05858269

Reaction notes

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