Water → HCID 135689626, compound

HRID 434724Notes

Reaction equation

HRID 434724 reaction equation
O.[NH2:2][C:3]1[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[C:6]([OH:14])=[CH:5][CH:4]=1.[CH:15](=O)[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18]>C(OCC)(=O)C>[CH3:13][C:10]1([CH3:12])[CH2:9][C:8]2[C:3]([N:2]=[CH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[OH:18])=[CH:4][CH:5]=[C:6]([OH:14])[C:7]=2[O:11]1

Participants

5

Reactant 3

HCID 962Water2×HCID 6998SalicylaldehydeHCID 15847236HCID 15847236, compound

Product 1

HCID 135689626HCID 135689626, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 500 milliliter round bottom flask equipped with a water collector, water condenser, magnetic stirrer and drying tube was added 5.38 grams (0.030 moles) of 4-amino-2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran, 3.91 grams (0.032 moles) of salicylaldehyde and 300 milliliters of ethyl acetate. The resulting reaction mixture was heated to reflux with removal of the first 50 milliliters of distillate, and the remaining mixture allowed to reflux for 1 additional hour with continuous stirring. After the stirring and refluxing period, the reaction mixture was cooled to room temperature, filtered, dried over magnesium sulfate and concentrated under reduced pressure to give 6.15 grams (0.022 moles) of 2,3-dihydro-2,2-dimethyl-4-(2-hydroxybenzylideneamino)benzofuran-7-ol in the form of a dark red oil.

Workup

  1. customdrying tube
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureto reflux with removal of the first 50 milliliters of distillate, and the remaining mixture
  5. temperatureto reflux for 1 additional hour with continuous stirring
  6. temperatureAfter the stirring and refluxing period
  7. filtrationfiltered
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1e0958bcb2b45cea1a5f2eeda8dee6c
Source dataset
uspto-grants-1983_08
Patent number
US04399148

Reaction notes

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