Water → HCID 19775615, compound

HRID 1613255Notes

Reaction equation

HRID 1613255 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][OH:11].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.O>C1C=CC=CC=1>[CH3:16][S:17]([O:11][CH2:10][CH:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:12][CH2:13][CH2:14][CH3:15])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12343352HCID 12343352, compound

Product 1

HCID 19775615HCID 19775615, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 24.7 g (0.1 mole) of the 2-(2,4-dichlorophenyl)hexan-1-ol and 13.8 g (0.12 mole) of methane sulfonyl chloride in 200 ml of benzene at 10° is slowly added 14.2 g (0.14 mole) of triethylamine. When the addition is complete the reaction is stirred and allowed to come up to ambient temperature over 1/2 hour period. The reaction slurry is then heated to reflux for 1/2 hour, cooled and poured into water. The organic solution is washed with dilute HCl then with water and finally with dilute sodium bicarbonate solution. After drying over anhydrous MgSO4, the benzene is stripped off to give 31.8 g (98%) of the crude product. This material is identified by ir and nmr. The purity is determined by glc.

Workup

  1. customat 10°
  2. additionWhen the addition
  3. temperatureThe reaction slurry is then heated
  4. temperatureto reflux for 1/2 hour
  5. temperaturecooled
  6. washThe organic solution is washed with dilute HCl
  7. dry with materialAfter drying over anhydrous MgSO4

Sources & evidence

ORD record
ord-ec8e04406e964a3f91458a218312174e
Source dataset
uspto-grants-1993_03
Patent number
US05192783

Reaction notes

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