Benzenesulfonyl chloride → HCID 21704973, compound

HRID 1595529Notes

Reaction equation

HRID 1595529 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][OH:18])=[CH:14][CH:13]=1.C(N([CH2:26][CH3:27])CC)C>ClCCl>[C:1]1([S:7]([O:18][CH2:17][CH2:16][C:15]2[CH:19]=[CH:20][C:12]([O:11][S:7]([C:27]3[CH:26]=[CH:3][CH:2]=[CH:1][CH:6]=3)(=[O:9])=[O:8])=[CH:13][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10393Tyrosol

Product 1

HCID 21704973HCID 21704973, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

42.2 g (240 mmole) benzenesulfonyl chloride in dichloromethane was slowly added to a solution of 15 g (108 mmole) 4-hydroxyphenethyl alcohol and 24.3 g (240 mmole) triethylamine in 120 ml dichloromethane at 0° C. After stirring at 0° C. to room temperature the starting material was consumed, water was added, the phases were separated and the organic phase was evaporated in vacuo. Diisopropyl ether was added, two phases were formed, the diisopropyl ether phase was decanted off and the rest of solvent was evaporated to give 32.65 g (yield 73%) of 4-[phenylsulfonyloxy]phenethyl 1-benzenesulfonate.

Workup

  1. customwas consumed
  2. additionwater was added
  3. customthe phases were separated
  4. customthe organic phase was evaporated in vacuo
  5. additionDiisopropyl ether was added
  6. customtwo phases were formed
  7. customthe diisopropyl ether phase was decanted off
  8. customthe rest of solvent was evaporated

Sources & evidence

ORD record
ord-f60b4770cad6420bb08747ac4c531423
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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