Water → Toluene-4-sulfonic acid 3-(4-chloro-phenyl)-prop-2-ynyl ester

HRID 992448Notes

Reaction equation

HRID 992448 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[K+].O>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][O:11][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 41117183-(4-Chlorophenyl)prop-2-yn-1-ol

Product 1

HCID 54290153Toluene-4-sulfonic acid 3-(4-chloro-phenyl)-prop-2-ynyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

To a mixture of 3-(4-chloro-phenyl)-prop-2-yn-1-ol (3.3 g) and toluene-4-sulfonyl chloride (3.7 g) in diethyl ether (100 ml) which is pre-cooled to −15° C. is added powdered potassium hydroxide (2.8 g) in small portions during 10 minutes. The reaction mixture is stirred at 0° C. during 90 minutes. Then water (200 ml) is added and the mixture is extracted with diethyl ether (2×100 ml) and washed with brine (50 ml). The organic layers are collected, dried (Na2SO4) and evaporated. Toluene-4-sulfonic acid 3-(4-chloro-phenyl)-prop-2-ynyl ester is obtained.

Workup

  1. extractionthe mixture is extracted with diethyl ether (2×100 ml)
  2. washwashed with brine (50 ml)
  3. customThe organic layers are collected
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ce6eab0715a7409c9005f963159ba39f
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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