Ethanol → HCID 18626557, compound

HRID 1859764Notes

Reaction equation

HRID 1859764 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:18]([OH:20])C.C=O.C([O-])([O-])=O.[K+].[K+]>O>[OH:17][CH2:16][C:6]1([CH2:18][OH:20])[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH:10]=[CH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]1=2

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 12435360HCID 12435360, compound

Product 1

HCID 18626557HCID 18626557, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 11 g (0.05 mol) of 5H-dibenzo[a,d]cycloheptene-5-carboxaldehyde (prepared according to L. SALISBURY, J. Org. Chem., 1972, 37, 4075), 66 ml of ethanol, 16.2 ml (0.2 mol) of aqueous 37% formaldehyde solution, 11 ml of water and 6.6 g (0.05 mol) of K2CO3 is refluxed for 20 hours. The reaction medium is then poured into 1 liter of water with stirring and the mixture is extracted with CH2Cl2. The combined organic phases are dried over Na2SO4 and evaporated. The residual mass is triturated from 60 ml of absolute ethanol and disperses as a beige-coloured solid, which is filtered off and dried. 5 g of product are obtained (yield: 40%).

Workup

  1. temperatureis refluxed for 20 hours
  2. extractionthe mixture is extracted with CH2Cl2
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customThe residual mass is triturated from 60 ml of absolute ethanol and disperses as a beige-coloured solid, which
  6. filtrationis filtered off
  7. customdried

Sources & evidence

ORD record
ord-b0490a01ec1d41358b9697b2952808ba
Source dataset
uspto-grants-2003_03
Patent number
US06528538B1

Reaction notes

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