Acetic Acid → HCID 54234370, compound

HRID 1732980Notes

Reaction equation

HRID 1732980 reaction equation
[C:1]([OH:4])(=O)[CH3:2].O.[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1>[OH-].[K+].C(O)C.C(=O)C>[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=[CH:2][CH:1]=[O:4])=[CH:15][C:10]=2[O:9][CH2:8][CH2:7]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehyde

Product 1

HCID 54234370HCID 54234370, compound

Reagents, catalysts & solvents 3

HCID 177AcetaldehydeSolvent2×HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution which is 5 molar in 2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde of formula XXVII ##STR19## and 0.58 molar in potassium hydroxide in ethanol as the solvent is added acetaldehyde in an amount sufficient to make the solution nominally 4 molar in acetaldehyde, over a period of 20 minutes and while stirring at 10° C. After the mixture is stirred at 10° C. for an additional 10 minutes, it is acidified by the addition of glacial acetic acid. Water is then added and the insoluble oil formed is extracted with ether. The ether solution is washed with water, dried and distilled to yield 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-propenal of formula XXVIII ##STR20##

Workup

  1. stirringAfter the mixture is stirred at 10° C. for an additional 10 minutes
  2. customthe insoluble oil formed
  3. extractionis extracted with ether
  4. washThe ether solution is washed with water
  5. customdried
  6. distillationdistilled

Sources & evidence

ORD record
ord-c2a9fe05aead4469af697221f25a1735
Source dataset
uspto-grants-1980_12
Patent number
US04239908

Reaction notes

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