4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

HRID 1196632Notes

Reaction equation

HRID 1196632 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.[OH:12]CCC1CC2C(C)=C(OCC3C=CC=CC=3)C(C)=C(C)C=2O1>>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([OH:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21781545HCID 21781545, compound

Product 1

HCID 6101p-Toluenesulfonic acidYield 177.9%

Conditions

Temperature
0 °C

Procedure

105 mg of p-toluenesulfonyl chloride is added to a solution of 156 mg of 2-(RS)-(2-hydroxyethyl)-2,3-dihydro-5-benzyloxy-4,6,7 -trimethylbenzofurane in 0.5 ml cooled to 0° C. The reaction mixture is stirred for 3 hours, then it is acidified and extracted. The organic extracts are dried and evaporated, thus giving 185 mg of raw product, which is then purified with chromatography (SiO2). 153 mg of p-toluenesulfonate of 2[2,3-dihydro-5-benzyloxy-4,6,7-trimethyl-2-(RS)benzofuranyl]ethyl are obtained. IR (KBr): 1359, 1177 cm-1 (νSO2). The product thus obtained is then solubilized in 2 ml of anhydrous tetrahydrofurane and added to a suspension of 45 mg of lithium and aluminum hydride in 5 ml of anhydrous tetrahydrofurane. The reaction mixture is stirred in an inert atmosphere for 30 minutes. The reaction process is carried out using the same procedure described in example 1. 82 mg of a white solid are obtained. m.p. 65°-67° C. IR (KBr): 1595 (νC--C), 1237 cm-1 (νC--O--C); 1H-NMR (CDCl3): δ 7.5-7.1 (5H,m), 4.8-4.4 (1H,m), 4.7 (2H,s), 3.3-2.5 (2H,m), 2.2 (6H,s), 2.1 (3H,s), 1.9-1.5 (2H,m), 1.0-(3H,t).

Workup

  1. extractionextracted
  2. customThe organic extracts are dried
  3. customevaporated
  4. customthus giving 185 mg of raw product, which
  5. customis then purified with chromatography (SiO2)

Sources & evidence

ORD record
ord-477e417c070f4f81be9c8e60a10f9083
Source dataset
uspto-grants-1992_05
Patent number
US05114966

Reaction notes

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