Water → HCID 14580197, compound

HRID 2372651Notes

Reaction equation

HRID 2372651 reaction equation
Br[CH2:2][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([OH:14])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[I-:21].[Na+].O.CCOCC>CC(C)=O>[I:21][CH2:2][C:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([OH:14])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 14580196HCID 14580196, compound

Product 1

HCID 14580197HCID 14580197, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-2-phenyl-3-phenylsulphonyl-2-propanol (1.3 g, 0.004 mole) is dissolved in acetone (30 cc). Sodium iodide (0.9 g, 0.006 mole) is added and heated under reflux for 15 h. The reaction mixture is poured into water (100 cc), reextracted with ether (3×50 cc), washed with a 15% strength NaHSO3 solution (50 cc) and then with water (50 cc) and is dried over MgSO4. The crystallized crude (0.9 g) is recrystallized from carbon tetrachloride to give yellow crystals of 1-iodo-2-phenyl-3-phenylsulphonyl-2-propanol (0.5 g, 31%). Mp=98° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 h
  3. washwashed with a 15% strength NaHSO3 solution (50 cc)
  4. dry with materialwith water (50 cc) and is dried over MgSO4
  5. customThe crystallized crude (0.9 g)
  6. customis recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-007255a8742c4521bb9d399cfc1871cc
Source dataset
uspto-grants-1992_03
Patent number
US05100460

Reaction notes

Loading…