Ethylene Glycol → HCID 21313220, compound

HRID 1679135Notes

Reaction equation

HRID 1679135 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 of 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-2955a7882e3d43c8b753334405ec6b63
Source dataset
uspto-grants-1978_03
Patent number
US04079062

Reaction notes

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