Benzene → HCID 20319762, compound

HRID 596519Notes

Reaction equation

HRID 596519 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]2[C:8](=[O:17])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.C1C=CC=CC=1.C(N(CC)CC)C.[CH3:39][CH2:40][O:41]CC>O.C(#N)C.C(O)CO>[CH2:39]1[CH2:40][O:41][C:8]2([C:7]3[CH:18]=[CH:19][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]2=3)[O:17]1

Participants

9

Reactant 5

HCID 241BenzeneHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 20319760HCID 20319760, compound

Product 1

HCID 20319762HCID 20319762, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.50 Gm. of 2-acetyl-5H-dibenzo[a,d]cycloheptene-5-one and 0.45 gm. of phosphorus pentachloride are stirred in 50 ml. of dry benzene for one hour, and then the solution is added to a mixture of 1.01 gm. of triethylamine, 1.35 gm. of ethylene glycol and 100 ml. of acetonitrile. The mixture is stirred for 20 hours then added to water and ether. The ethereal layer is washed with water, dried and evaporated to give a nearly quantitative yield of 5,5-ethylenedioxy-2-acetyl-5H-dibenzo[a,d]cycloheptene.

Workup

  1. additionthe solution is added to a mixture of 1.01 gm
  2. washThe ethereal layer is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-690d817d64e1426185596f47f0ac3bc0
Source dataset
uspto-grants-1977_03
Patent number
US04011241

Reaction notes

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