Pyridine → Diisopropyl Ether

HRID 1730174Notes

Reaction equation

HRID 1730174 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:10][OH:11].[S:21](Cl)([CH3:24])(=[O:23])=[O:22].N1C=C[CH:29]=[CH:28][CH:27]=1>>[CH:28]([O:22][CH:18]([CH3:17])[CH3:13])([CH3:29])[CH3:27].[CH3:24][S:21]([O:11][CH2:10][CH:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 12391216HCID 12391216, compound

Product 2

HCID 7914Diisopropyl EtherHCID 54131299HCID 54131299, compound

Procedure

To a stirred solution of 48.2 parts of 2,3-bis(2,4-dichlorophenyl)-1-propanol in 150 parts of pyridine are added dropwise 14 parts of mesyl chloride at room temperature. Upon completion, stirring at room temperature is continued overnight. The reaction mixture is poured onto water and the product is extracted twice with diisopropylether. The combined extracts are washed successively three times with a dilute hydrochloride acid solution and once with water, dried, filtered and evaporated. The residue is crystallized first from methanol and then from diisopropylether, yielding 25.8 parts of 2,3-bis(2,4-dichlorophenyl)-1-propanol methanesulfonate; mp. 84° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted twice with diisopropylether
  3. washThe combined extracts are washed successively three times with a dilute hydrochloride acid solution
  4. dry with materialonce with water, dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized first from methanol

Sources & evidence

ORD record
ord-9ce94970bb6149b4adc4d8f861c92460
Source dataset
uspto-grants-1976_11
Patent number
US03991201

Reaction notes

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