1-Butanol → Diisopropyl Ether

HRID 1390595Notes

Reaction equation

HRID 1390595 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[O:4].[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([O:24][CH2:25][CH:26]([OH:29])[CH2:27][OH:28])[CH:18]=[CH:17]2.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CCC>O.C1C=CC=CC=1>[CH:14]([O:4][CH:3]([CH3:2])[CH3:5])([CH3:15])[CH3:23].[CH2:25]([O:24][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:26][CH2:27][CH3:30].[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=2[Cl:12])[O:29][CH:26]([CH2:25][O:24][C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][CH:23]=[C:14]([Br:13])[CH:15]=3)[CH:20]=2)[CH2:27][O:28]1

Participants

9

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 20332693HCID 20332693, compound

Product 3

HCID 7914Diisopropyl EtherHCID 8909Butyl etherHCID 20332732HCID 20332732, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 13.6 parts of 2-bromo-2',4'-dichloroacetophenone, 18 parts of 3-(6-bromo-2-napthyloxy)-1,2-propanediol, 3 parts of p-toluenesulfonic acid, 80 parts of n-butanol and 180 parts of benzene is stirred and refluxed for 24 hours with water-separator. The reaction mixture is evaporated. The residue is dissolved in chloroform and the solution is stirred with silica gel for one hour. The latter is filtered off and the filtrate is evaporated. The residue is crystallized twice: first from diisopropylether and then from dibutylether, yielding A 2-(bromomethyl)-4-(6-bromo-2-naphthyloxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionThe residue is dissolved in chloroform
  3. stirringthe solution is stirred with silica gel for one hour
  4. filtrationThe latter is filtered off
  5. customthe filtrate is evaporated
  6. customThe residue is crystallized twice

Sources & evidence

ORD record
ord-d704adbc123c464b9c75ee8e65f3bcf7
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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