Menthol → 2-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfonate

HRID 909967Notes

Reaction equation

HRID 909967 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([OH:8])[CH:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.N12CCN(CC1)CC2.[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C(OCC)(=O)C>[CH:2]1([CH3:1])[CH2:3][CH2:4][CH:5]([CH:9]([CH3:11])[CH3:10])[CH:6]([O:8][S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:7]1

Participants

5

Reactant 3

HCID 1254MentholHCID 73974-Toluenesulfonyl chlorideHCID 9237Dabco

Product 1

HCID 5866292-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfonateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

7.8 g (0.05 mol) DL-menthol and 11.2 g (0.1 mol) 1,4-diazabicyclo[2.2.2]octane are added to 50 mL ethyl acetate. This solution is cooled in an ice bath and 14.3 g (0.075 mol) tosyl chloride in 30 mL ethyl acetate is added dropwise over 15 mins. The ice bath is removed and the mixture is allowed to stir at room temperature for 4 days. After this time the solid precipitate is filtered and washed. The ethyl acetate filtrate and washings are then combined and washed successively with 10% HCl, saturated aq NaHCO3 and brine. The ethyl acetate is then evaporated to yield 11.5 g (74%) of menthyl-p-toluenesulfonate.

Workup

  1. temperatureThis solution is cooled in an ice bath
  2. customThe ice bath is removed
  3. filtrationAfter this time the solid precipitate is filtered
  4. washwashed
  5. washwashed successively with 10% HCl, saturated aq NaHCO3 and brine
  6. customThe ethyl acetate is then evaporated

Sources & evidence

ORD record
ord-a42f888bd01549978e4c90b5894ed9b1
Source dataset
uspto-grants-2011_09
Patent number
US08021820B2

Reaction notes

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