Hydrochloric Acid → [(Chloromethyl)sulfanyl]cyclohexane

HRID 2288567Notes

Reaction equation

HRID 2288567 reaction equation
C=O.[ClH:3].[CH:4]1([SH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:11](=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:3][CH2:11][S:10][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 15290Cyclohexanethiol

Product 1

HCID 20026068[(Chloromethyl)sulfanyl]cyclohexane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
40 °C

Procedure

Into a 1 L four necked flask equipped with a nitrogen supply tube, a stirrer and a thermometer, 12.1 g of paraformaldehyde and 60 g of toluene were mixed and stirred, and then 120 mL of concentrated hydrochloric acid was added thereto. Thereafter, the reaction solution was heated to 40° C., and 60 g of a toluene solution containing 35.4 g of cyclohexanethiol was added over a period of 20 minutes. After completion of the dropwise addition, the reaction solution was stirred while maintaining it at 50° C. After confirming the completion of the reaction by TLC, the water phase was discharged, and the organic phase was made alkaline with a saturated sodium carbonate aqueous solution to obtain a toluene solution of chloromethylcyclohexylsulfide.

Workup

  1. additionwas added over a period of 20 minutes
  2. additionAfter completion of the dropwise addition
  3. stirringthe reaction solution was stirred
  4. temperaturewhile maintaining it at 50° C
  5. customthe completion of the reaction by TLC

Sources & evidence

ORD record
ord-7bfe407d33dc43539907f0bb41eae341
Source dataset
uspto-grants-2000_07
Patent number
US06090518

Reaction notes

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