Toluene → Methanone, phenyl(4-phenyl-1,3-dioxolan-4-yl)-

HRID 616047Notes

Reaction equation

HRID 616047 reaction equation
[CH2:1]([C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([OH:12])[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:2].[C:19]1(C)C=CC=CC=1>>[C:4]([C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:1][O:2][CH2:19][O:12]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-one

Product 1

HCID 3089168Methanone, phenyl(4-phenyl-1,3-dioxolan-4-yl)-

Procedure

About 273 grams of crude, wet α-methylolbenzoin prepared as described in Example I was refluxed under a Dean-Stark trap with 0.50 liters toluene for about two hours to remove about 50 ml. water. The reaction mixture was allowed to cool and 35 grams paraformaldehyde and 10 grams p-toluenesulfonic acid were added. The reaction mixture was heated for 45 minutes under controlled conditions such that the solvent refluxed below the trap and no water was collected. The temperature of the reaction mixture was then increased and about 16 ml. water was collected over a three-hour period. The mixture was allowed to cool and then saturated with ammonia gas. The resulting salt precipitate was removed by filtration and benzene solvent removed under vacuum from the residual yellow solution containing the solid reaction product. The crude solid reaction product was recrystallized from 1.6 l. of boiling hexane. 156 grams of recrystallized produce having m.p. of 66°-66.5° C was obtained.

Workup

  1. customto remove about 50 ml
  2. temperatureto cool
  3. addition35 grams paraformaldehyde and 10 grams p-toluenesulfonic acid were added
  4. temperatureThe reaction mixture was heated for 45 minutes under controlled conditions such that the solvent
  5. temperaturerefluxed below the trap
  6. customno water was collected
  7. temperatureThe temperature of the reaction mixture was then increased
  8. customwater was collected over a three-hour period
  9. temperatureto cool
  10. customThe resulting salt precipitate was removed by filtration and benzene solvent
  11. customremoved under vacuum from the residual yellow solution
  12. additioncontaining
  13. customthe solid reaction product
  14. customThe crude solid reaction product
  15. customwas recrystallized from 1.6 l
  16. custom156 grams of recrystallized
  17. customproduce
  18. customwas obtained

Sources & evidence

ORD record
ord-5475a0e1d3544e15a9fbd459db803444
Source dataset
uspto-grants-1978_02
Patent number
US04072694

Reaction notes

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