Toluene → 2,2-Bis(4-fluorophenyl)-4-(chloromethyl)-1,3-dioxolane

HRID 345573Notes

Reaction equation

HRID 345573 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[Cl:17][CH2:18][CH:19]([OH:22])[CH2:20]O.O.CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[O:22][CH:19]([CH2:18][Cl:17])[CH2:20][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 72903-Chloro-1,2-propanediolHCID 95824,4'-DifluorobenzophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 198834602,2-Bis(4-fluorophenyl)-4-(chloromethyl)-1,3-dioxolaneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 10 parts of bis(4-fluorophenyl)methanone, 22.1 parts of 3-chloro-1,2-propanediol, 0.2 parts of 4-methylbenzenesulfonic acid hydrate and 90 parts of methylbenzene was stirred and refluxed for 23 hours using a water-separator. The reaction mixture was poured onto alkaline water. Upon stirring, the layers were separated. The organic phase was washed with alkaline water, dried, filtered and evaporated, yielding 14 parts (100%) of 2,2-bis(4-fluorophenyl)-4-(chloromethyl)-1,3-dioxolane as a residue (intermediate 99).

Workup

  1. temperaturerefluxed for 23 hours
  2. stirringUpon stirring
  3. customthe layers were separated
  4. washThe organic phase was washed with alkaline water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-034ff43636804d908979daf750cc8aa6
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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