Methanol → 2-formyl 5H-dibenzo[a,d] cyclohepten5-one

HRID 596518Notes

Reaction equation

HRID 596518 reaction equation
CO.C(N(CC)CC)C.[CH:10]1[C:20]2[CH:19]=[CH:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[C:15](=[O:25])[C:14]=2[CH:13]=[CH:12][C:11]=1[C:26](OC)=[O:27].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O.CCOCC>[CH:26]([C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:25])[C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[CH:18]=[CH:19][C:20]=2[CH:10]=1)=[O:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 203106812-carbomethoxy-5-oxo-5H-dibenzo[a,d]cyclohepteneHCID 21226445Aluminium lithium hydride

Product 1

HCID 203197612-formyl 5H-dibenzo[a,d] cyclohepten5-oneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The acid chloride from Preparation 3A is converted to the methyl ester by reaction with methanol and triethylamine. 2.0 Gm. of methyl 5H-dibenzo[a,d]cyclohepten-5-one-2-carboxylate is dissolved in 200 ml. of ether and 0.5 gm. of lithium aluminium hydride is added. The reaction is refluxed for two hours then cooled and the excess reducing agent is decomposed by addition of water. The solution is filtered and to the filtrate is added 15.0 gm. of manganese dioxide. The mixture is stirred for 16 hours then filtered and evaporated to give a 50% yield of 2-formyl 5H-dibenzo[a,d] cyclohepten5-one, m.p. 149°-152° C.

Workup

  1. temperatureThe reaction is refluxed for two hours
  2. temperaturethen cooled
  3. filtrationThe solution is filtered and to the filtrate
  4. additionis added 15.0 gm
  5. filtrationthen filtered
  6. customevaporated

Sources & evidence

ORD record
ord-7f534e3301a04901a51d69bf082dd92f
Source dataset
uspto-grants-1977_03
Patent number
US04011241

Reaction notes

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