Chlorosulfonic acid → HCID 63822588, compound

HRID 630615Notes

Reaction equation

HRID 630615 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]#[CH:8]>ClCCl>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:12][CH:11]=1)[C:7]#[CH:8]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 83613(Prop-2-ynyloxy)benzene

Product 1

HCID 63822588HCID 63822588, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Referring to FIG. 39, chlorosulfonic acid (19.9 mL, 0.299 mol) was added dropwise to (prop-2-yn-1-yloxy)benzene (17.2 g, 0.130 mol) in dichloromethane (100 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour and then poured into ice-water and extracted with dichloromethane. The extract was washed with water, dried (MgSO4), and evaporated. The residue was purified by Biotage flash column chromatography (30% EtOAc/Hep) to give product as an oil (17.9 g, 60%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by Biotage flash column chromatography (30% EtOAc/Hep)

Sources & evidence

ORD record
ord-224d31633559482a8491a7f28daba350
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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