4-Methoxybenzenesulfonyl chloride → HCID 21705015, compound

HRID 1595487Notes

Reaction equation

HRID 1595487 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(N([CH2:16][CH3:17])CC)C.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>ClCCl>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:2]([O:1][S:26]([C:17]3[CH:16]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)(=[O:28])=[O:27])=[CH:3][CH:4]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10393Tyrosol

Product 1

HCID 21705015HCID 21705015, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.76 g (20 mmole) p-hydroxyphenethyl alcohol was dissolved in 80 ml dichloromethane. 6 g triethylamine, 8.5 g (41 mmole) 4-methoxybenzenesulfonyl chloride and 0.2 g 4-dimethyl-aminopyridine were added. The mixture was stirred over night at room temperature and filtered through silica gel with dichloromethane as eluent to give 8.5 g (yield 89%) of 4-(4-methoxyphenylsulfonyloxy)phenethyl 4-methoxy-1-benzenesulfonate.

Workup

  1. filtrationfiltered through silica gel with dichloromethane as eluent

Sources & evidence

ORD record
ord-e307fae0d65d4fcb88beb4d321a64669
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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