Toluene → HCID 20332745, compound

HRID 1706889Notes

Reaction equation

HRID 1706889 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:13])(O)[CH3:11])=[CH:4][CH:3]=1.[Br:14][CH2:15][C:16]1([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])OCC[O:17]1.CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1>O.C(O)CCC>[Br:14][CH2:15][C:16]1([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[O:13][CH:10]([CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH2:11][O:17]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 1089062-(Bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolaneHCID 20332775HCID 20332775, compound

Product 1

HCID 20332745HCID 20332745, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of 14.4 parts of 1-[2-(4-methylphenyl)ethyl]-ethanediol, 15.6 parts of 2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane, 5 parts of 4-methylbenzenesulfonic acid, 225 parts of methylbenzene and 40 parts of butanol is stirred and refluxed for 3 days with water-separator. The reaction mixture is evaporated and the residue is dissolved in 2,2'-oxybispropane: The solution is stirred for 30 minutes with silica gel. The latter is filtered off and the filtrate is evaporated, yielding 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-[2-(4-methylphenyl)ethyl]-1,3-dioxolane as a residue.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in 2,2'-oxybispropane
  3. stirringThe solution is stirred for 30 minutes with silica gel
  4. filtrationThe latter is filtered off
  5. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-10f8c81214c2489b8b3478633c334208
Source dataset
uspto-grants-1980_06
Patent number
US04209447

Reaction notes

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