Water → alpha-Cyano-m-phenoxybenzyl mesylate

HRID 2049823Notes

Reaction equation

HRID 2049823 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].[CH2:21]([N:23](CC)CC)C.O>CCOCC>[CH3:16][S:17]([O:12][CH:11]([C:21]#[N:23])[C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 20482835alpha-Cyano-m-phenoxybenzyl mesylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

The cyanohydrin of m-phenoxybenzaldehyde (8.5 g, 0.038 mol) is dissolved in 150 ml ether and cooled to 0° in an ice bath. To this is slowly added methanesulfonyl chloride in 20 ml ether. The mixture is stirred for 10 min, then triethylamine in 20 ml ether is added dropwise. The solution turns white, and a precipitate appears. The reaction mixture is kept at 0° overnight and is then worked up with water and extracted with ether. The ether phase is washed with 30% sodium bisulfite solution (2X), ether and water (2X), and dried over sodium sulfate. The mixture is filtered and the filtrate concentrated to give α-cyano-m-phenoxybenzyl methanesulfonate.

Workup

  1. temperaturecooled to 0° in an ice bath
  2. waitThe reaction mixture is kept at 0° overnight
  3. extractionextracted with ether
  4. washThe ether phase is washed with 30% sodium bisulfite solution (2X), ether and water (2X)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe mixture is filtered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d29b36bbfcba4bf3b58c01b0c38eed90
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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