Water → HCID 13409934, compound

HRID 461991Notes

Reaction equation

HRID 461991 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[OH:18][CH2:19][C:20]12[CH2:27][CH2:26][C:23]([CH3:28])([CH2:24][CH2:25]1)[CH2:22][CH2:21]2.O>C(OCC)(=O)C>[S:7]([O:18][CH2:19][C:20]12[CH2:25][CH2:24][C:23]([CH3:28])([CH2:26][CH2:27]1)[CH2:22][CH2:21]2)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 13227648(4-Methylbicyclo[2.2.2]octan-1-yl)methanol

Product 1

HCID 13409934HCID 13409934, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.156 Mole of p-toluenesulfonyl chloride is dissolved in 150 ml. of anhydrous pyridine at 0° C, under nitrogen, and then 0.078 mole of 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane is added slowly and the mixture then stirred for two hours. 2 Ml. of water is then added and the mixture stirred for five minutes and then poured into 600 ml. of ethyl acetate. The organic phase is washed twice with water, then washed with 2 Normal aqueous hydrochloric acid until no more pyridine remains. The ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate is then evaporated under vacuum affording 4-methylbicyclo[2.2.2]oct-1-yl methanol tosylate.

Workup

  1. stirringthe mixture stirred for five minutes
  2. additionpoured into 600 ml
  3. washThe organic phase is washed twice with water
  4. washwashed with 2 Normal aqueous hydrochloric acid until no more pyridine
  5. washThe ethyl acetate solution is then washed with aqueous saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate is then evaporated under vacuum

Sources & evidence

ORD record
ord-0ff7fa2053b74a048e96ebce373ac3e3
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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