Ethylene Glycol → HCID 21313220, compound

HRID 971642Notes

Reaction equation

HRID 971642 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:16])[CH3:15].[Br:17]Br.[CH2:19]([OH:22])[CH2:20]O.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)CCC.O.C1C=CC=CC=1>[Br:17][CH2:15][C:14]1([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C:13]=3[CH:1]=2)[O:22][CH2:19][CH2:20][O:16]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 24408Bromine2×HCID 699082-Acetylfluorene

Product 1

HCID 21313220HCID 21313220, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

20.8 parts of 1-(9H-fluoren-2-yl)ethanone are dissolved in 240 parts of butanol. At a temperature pf 50° C., 16 parts of bromine are added dropwise while the mixture is allowed to reach room temperature. After complete addition of bromine (1 hour), the whole is stirred at room temperature for 1 hour. Then there are added successively 7.5 parts of 1,2-ethanediol, 360 parts of benzene and 2 parts of 4-methylbenzenesulfonic acid. Stirring is continued overnight at reflux temperature with water-separator. After cooling to room temperature, the reaction mixture is evaporated. The residue is taken up in a mixture of 2,2'-oxybispropane and benzene (1:1 by volume). The resulting solution is washed successively with a diluted sodium hydroxide solution and three times with water, dried, filtered and evaporated. The residue is crystallized from methanol. The product is filtered off and dried, yielding 20.5 parts (62%) of 2-(bromomethyl)-2-(9H-fluoren-2-yl)-1,3-dioxolane; mp. 90° C.

Workup

  1. customto reach room temperature
  2. stirringStirring
  3. waitis continued overnight
  4. temperatureAfter cooling to room temperature
  5. customthe reaction mixture is evaporated
  6. additionThe residue is taken up in a mixture of 2,2'-oxybispropane and benzene (1:1 by volume)
  7. washThe resulting solution is washed successively with a diluted sodium hydroxide solution and three times with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is crystallized from methanol
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-882d97b4f7ed4d9da30347e1c580c6c8
Source dataset
uspto-grants-1979_07
Patent number
US04160838

Reaction notes

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