Methanesulfonyl chloride → (+/-)-2-[4-(4-Chlorophenoxy)-phenoxyl]-propyl mesylate

HRID 263082Notes

Reaction equation

HRID 263082 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH:17]([CH3:20])[CH2:18][OH:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[S:2]([O:19][CH2:18][CH:17]([O:16][C:15]1[CH:21]=[CH:22][C:12]([O:11][C:10]2[CH:23]=[CH:24][C:7]([Cl:6])=[CH:8][CH:9]=2)=[CH:13][CH:14]=1)[CH3:20])(=[O:4])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 128048842-[4-(4-Chlorophenoxy)-phenoxy]-propanol

Product 1

HCID 21318102(+/-)-2-[4-(4-Chlorophenoxy)-phenoxyl]-propyl mesylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.1 g (0.07 mol) of methanesulphonyl chloride are run, at about 10° C., into a solution of 19.5 g (0.07 mol) of (±)-2-[4-(4-chlorophenoxy)-phenoxy]-1-propanol (CRL 40 300) prepared as indicated in Example 27, in 35 ml of pyridine. The reaction mixture is stirred for 1 hour at ambient temperature and is poured onto ice. The insoluble matter is extracted with diethyl ether and the organic phase obtained is washed with dilute hydrochloric acid and dried, to give a white pasty residue after evaporation of the solvent. The solidification of this residue is petroleum ether gives 24 g of a white powder which is insoluble in water.

Workup

  1. customprepared
  2. additionis poured onto ice
  3. extractionThe insoluble matter is extracted with diethyl ether
  4. customthe organic phase obtained
  5. washis washed with dilute hydrochloric acid
  6. customdried
  7. customto give a white pasty residue
  8. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-916fbce462c146048378183b60ff8d7f
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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