Ethylene Glycol → HCID 22750660, compound

HRID 1606130Notes

Reaction equation

HRID 1606130 reaction equation
[C:1]([C:4]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:2][C:1]1([C:4]2[C:14]3[CH2:13][CH2:12][C:11]4[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=4[C:9](=[O:19])[C:8]=3[CH:7]=[CH:6][CH:5]=2)[O:22][CH2:21][CH2:20][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 22750665HCID 22750665, compound

Product 1

HCID 22750660HCID 22750660, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.4 g. of 1-acetyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 9.5 g. of ethylene glycol, 30 ml. of toluene and 60 mg. of p-toluenesulfonic acid are heated in a water separator at reflux for 8 hours. Thereafter, the mixture is concentrated under reduced pressure, taken up in ethyl acetate, washed with sodium carbonate solution and water, dried and evaporated, whereby 1-(2-methyl-1,3-dioxolan-2-yl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one is obtained as yellow crystals having a melting point of 144°-145°C. (from ethyl acetate/petroleum ether).

Workup

  1. temperatureat reflux for 8 hours
  2. concentrationThereafter, the mixture is concentrated under reduced pressure
  3. washwashed with sodium carbonate solution and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-c19244da3c0e499c97c8e8b90a5b95e0
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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