Methanesulfonyl chloride → 1-Benzyloxy-4-(2-methanesulfonyloxyethyl)benzene

HRID 978231Notes

Reaction equation

HRID 978231 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][OH:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C.N1C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][O:20][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:21][CH:22]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3017260p-(Benzyloxy)phenethyl alcohol

Product 1

HCID 115004941-Benzyloxy-4-(2-methanesulfonyloxyethyl)benzeneYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.51 g of methanesulfonyl chloride in 5 ml of diethyl ether was added dropwise over a period of 0.5 hour to a stirred solution of 7.0 g of 4-benzyloxyphenethyl alcohol in 20 ml of pyridine at 0° C. Stirring was continued for 2 hours while the mixture was allowed to warm to room temperature. The mixture was then partitioned between 150 ml of 2N hydrochloric acid and dichloromethane. The organic phase was separated, washed with water, dried over sodium sulfate, filtered, and evaporated. Trituration of the residue with n-hexane brought about crystallization. The crystals were removed by filtration and dried, whereby 8.9 g (95%) of 1-benzyloxy-4-(2-methanesulfonyloxyethyl)benzene having a melting point of 60°-64° C. were obtained.

Workup

  1. customThe mixture was then partitioned between 150 ml of 2N hydrochloric acid and dichloromethane
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customTrituration of the residue with n-hexane brought about crystallization
  8. customThe crystals were removed by filtration
  9. customdried

Sources & evidence

ORD record
ord-96e1c929ce9c49218a7bd3c1dd4b6a19
Source dataset
uspto-grants-1987_05
Patent number
US04663462

Reaction notes

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