Methanol → HCID 21409392, compound

HRID 1283678Notes

Reaction equation

HRID 1283678 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH3:16])[CH:14]=[O:15])=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.[CH3:21]O.[O:23]1CCC[CH2:24]1.O>Cl(O)(=O)(=O)=O.N1C=CC=CC=1.CCOCC>[CH3:21][O:15][CH:14]([O:23][CH3:24])[CH:13]([C:11]1[CH:10]=[CH:9][C:8]2[C:2](=[O:1])[C:3]3[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=3[CH:5]=[CH:6][C:7]=2[CH:12]=1)[CH3:16]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 214093832-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propanal

Product 1

HCID 21409392HCID 21409392, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 24247Perchloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

0.200 G. of 2-(5-oxo-5 -H-dibenzo[a,d]cyclohepten-2-yl)propanal is dissolved in 10 ml. of methanol and 20 ml. of tetrahydrofuran, and 1 drop of 60% aqueous perchloric acid is added. The mixture is left for 1 hour then 2 drops of pyridine are added and the mixture added to water and ether. The organic layer is washed with water, dried and evaporated and the residue chromatographed on 5 gm. of silica gel, eluting with 50:50:1 hexane:ether:triethylamine to afford 1,1-dimethoxy 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propane.

Workup

  1. washThe organic layer is washed with water
  2. customdried
  3. customevaporated
  4. customthe residue chromatographed on 5 gm
  5. washof silica gel, eluting with 50:50:1 hexane

Sources & evidence

ORD record
ord-0022a1f6886e4afabef0c1290f4f6875
Source dataset
uspto-grants-1976_08
Patent number
US03975540

Reaction notes

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