Hydrochloric Acid → 4-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

HRID 24932Notes

Reaction equation

HRID 24932 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>ClCCl>[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([O:7][CH2:8][C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 50337133-(4-Nitrophenyl)prop-2-yn-1-ol

Product 1

HCID 225692544-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.4 ml (54 mmol) of pyridine are added dropwise to a solution of 5.8 g (33 mmol) of 4-(3-hydroxyprop-1-ynyl)-nitrobenzene and 5.2 g (27 mmol) of p-toluenesulphonic acid chloride in 50 ml of dichloromethane at 0° C. After 2 hours at 0° C. about 25 g of ice and 8 ml of conc. hydrochloric acid are added. The organic phase is separated off and washed with water. After removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product is obtained as an oil.

Workup

  1. customThe organic phase is separated off
  2. washwashed with water
  3. customAfter removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product
  4. customis obtained as an oil

Sources & evidence

ORD record
ord-609c1b4a63564df49883e9626a456c92
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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