1-Butanol → HCID 70590507, compound

HRID 1390593Notes

Reaction equation

HRID 1390593 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].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([O:21][CH2:22][CH:23]([OH:26])[CH2:24]O)[CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CCC>O.C1C=CC=CC=1>[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:26][CH:23]([CH2:22][O:21][C:16]2[CH:15]=[C:14]([Cl:13])[CH:19]=[CH:18][C:17]=2[CH3:20])[CH2:24][O:4]1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 21423644HCID 21423644, compound

Product 1

HCID 70590507HCID 70590507, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 6 parts of 2-bromo-2', 4'-dichloroacetophenone, 6 parts of 3-(4-chloro-o-tolyloxy)-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 solvent is removed in vacuo and the residue is triturated in methanol. The produce is filtered off and crystallized from petroleumether, yielding A + B 2-(bromomethyl)-4-(4-chloro-2-tolyloxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is triturated in methanol
  3. filtrationThe produce is filtered off
  4. customcrystallized from petroleumether

Sources & evidence

ORD record
ord-9724362e1c824d529ff84aff9b43a30a
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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