Water → alpha-Cyano-m-phenoxybenzyl mesylate

HRID 1855951Notes

Reaction equation

HRID 1855951 reaction equation
[C:1]([CH:3]([OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)#[N:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.O>CCOCC>[S:19]([O:17][CH:3]([C:1]#[N:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)(=[O:21])(=[O:20])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

Product 1

HCID 20482835alpha-Cyano-m-phenoxybenzyl mesylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

α-Cyano-m-phenoxybenzyl alcohol (8.5 g, 38 mmol) is dissolved in 150 ml ether and cooled in an ice-bath. To the solution is slowly added methanesulfonyl chloride (5.4 g, 47 mmol) in 20 ml ether. After the mixture is stirred about 20 minutes, triethylamine (4.76 g, 47 mmol) in 20 ml ether is added slowly and the mixture kept at 0° for 24 hours. Water is then added and the organic layer is separated, washed with 30% aqueous sodium bisulfite and water, dried and solvent removed under vacuum to yield α-cyano-m-phenoxybenzyl mesylate.

Workup

  1. temperaturecooled in an ice-bath
  2. waitthe mixture kept at 0° for 24 hours
  3. customthe organic layer is separated
  4. washwashed with 30% aqueous sodium bisulfite and water
  5. customdried
  6. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-5f6cc03fa67d45aa9ef8c74fbdb55c37
Source dataset
uspto-grants-1980_08
Patent number
US04217302

Reaction notes

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