Hydrochloric Acid → HCID 11459813, compound

HRID 1744716Notes

Reaction equation

HRID 1744716 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl>N1C=CC=CC=1>[S:9]([O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 155123-Cyclohexene-1-methanol

Product 1

HCID 11459813HCID 11459813, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL round bottom flask equipped with a stirring bar was charged with 67.2 g (0.60 mol) 3-cyclohexene-1-methanol, and 170 mL of pyridine. The mixture was cooled to 0° C. Tosyl chloride (120.8 g, 0.63 mol) was slowly added to above mixture at 0–5° C. The reaction was carried out for 3 hrs. The reaction mixture was poured into 1.2 L of HCl solution (1 M), extracted with chloroform (3×200 mL), washed with water (3×200 mL), dried with sodium sulfate. The solvent was evaporated and the residue distilled under vacuum to give a tosylate.

Workup

  1. customA 500 mL round bottom flask equipped with a stirring bar
  2. extractionextracted with chloroform (3×200 mL)
  3. washwashed with water (3×200 mL)
  4. dry with materialdried with sodium sulfate
  5. customThe solvent was evaporated
  6. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-caf1b54847704259ab1bb7ee714e271e
Source dataset
uspto-grants-2006_03
Patent number
US07018559B2

Reaction notes

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