3,4-Dihydroxybenzaldehyde → HCID 19973517, compound

HRID 374534Notes

Reaction equation

HRID 374534 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Br[C:12](Br)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]2[O:10][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:1][C:2]=2[CH:3]=1)=[O:6]

Participants

5

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester

Product 1

HCID 19973517HCID 19973517, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One equivalent of 3,4-dihydroxybenzaldehyde, 1.1 equivalents of diethyl dibromomalonate and powdered potassium carbonate is stirred in acetonitrile at room temperature for 18 hours. The reaction mixture is filtered, evaporated in vacuo and distilled to give diethyl 5-formyl-1,3-benzodioxole-2,2-dicarboxylate. 1H NMR(CDCl3): δ 9.9(s,1H,CHO); 7.5(m,2H, aromatic H) ; 7.1(d, 1H,aromatic H); 4.45(q,4H,CH2); 1.8(t,6H,CH3).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated in vacuo
  3. distillationdistilled

Sources & evidence

ORD record
ord-74aba02008b544af883ce90f12006a1b
Source dataset
uspto-grants-1996_01
Patent number
US05480908

Reaction notes

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