4-Toluenesulfonyl chloride → HCID 131718833, compound

HRID 1769802Notes

Reaction equation

HRID 1769802 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:10][CH2:11][OH:12].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:10][CH2:11][O:12][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20097358HCID 20097358, compound

Product 1

HCID 131718833HCID 131718833, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The propanol (XVII) of Example 3b) (35 g, 0.128 mol) in 100 ml chloroform containing 30 ml pyridine was cooled to about -10° and then treated with p-toluene sulphonyl chloride (29 g, 0.15 mol). After standing in the cooler (about +5° C.) overnight, the mixture was poured into ice-water, the organic phase was washed with water and cold 2N HCl, dried, and the solvent was distilled off at <50° C., giving a crude oil in quantitative yield. Recrystallization from IPE gave white crystals of low and indefinite m.p.

Workup

  1. customAfter standing in the cooler (about +5° C.) overnight
  2. washthe organic phase was washed with water and cold 2N HCl
  3. customdried
  4. distillationthe solvent was distilled off at <50° C.
  5. customgiving a crude oil in quantitative yield
  6. customRecrystallization from IPE
  7. customgave white crystals of low and indefinite

Sources & evidence

ORD record
ord-efb3b565c23a4ee7a26d9a27c7f8f95d
Source dataset
uspto-grants-1995_01
Patent number
US05382600

Reaction notes

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