Diisopropyl Ether → HCID 21499512, compound

HRID 1730176Notes

Reaction equation

HRID 1730176 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][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11].[CH3:19][S:20](Cl)(=[O:22])=[O:21].O(C(C)C)C(C)C>N1C=CC=CC=1>[CH3:19][S:20]([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:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 31297Methanesulfonyl chlorideHCID 12391219HCID 12391219, compound

Product 1

HCID 21499512HCID 21499512, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 15.8 parts of β-(2,4-dichlorophenyl)benzene-propanol, 12.15 parts of methanesulfonyl chloride, 50 parts of pyridine and 70 parts of 2,2'-oxybispropane is stirred overnight at room temperature. The reaction mixture is poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed twice with a diluted hydrochloric acid solution and once with water, dried, filtered and evaporated. The residue is triturated in methanol. The product is filtered off and crystallized from ethanol, yielding 7.28 parts of β-(2,4-dichlorophenyl)benzenepropanol methanesulfonate; mp. 87.3° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionthe product is extracted twice with 2,2'-oxybispropane
  3. washThe combined extracts are washed twice with a diluted hydrochloric acid solution and once with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is triturated in methanol
  8. filtrationThe product is filtered off
  9. customcrystallized from ethanol

Sources & evidence

ORD record
ord-b46bf84816f347d396878cb749215076
Source dataset
uspto-grants-1976_11
Patent number
US03991201

Reaction notes

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