Water → 2,3-Dihydroxy-1-naphthaldehyde

HRID 1070670Notes

Reaction equation

HRID 1070670 reaction equation
P(Cl)(Cl)(Cl)=O.[OH:6][C:7]1[C:16]([OH:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.O.CN([CH:22]=[O:23])C>>[OH:6][C:7]1[C:16]([OH:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[CH:22]=[O:23]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70912,3-DihydroxynaphthaleneHCID 24813Phosphorus oxychloride

Product 1

HCID 133438102,3-Dihydroxy-1-naphthaldehyde

Procedure

Phosphorous oxychloride (1.9 ml) was added to a solution of 2,3-dihydroxynaphthalene (3.2 g) in DMF (26 ml) at 0° C. The reaction mixture was kept for four hours at 100° C. Water (50 ml) was added to the cooled mixture and the resulting oily suspension refluxed for 20 min. The cool reaction mixture was poured into ice, filtered, washed with water and recrystallized from 2-propanol-water. Yield: 0.1 g, melting point 129-134° C.

Workup

  1. temperaturethe resulting oily suspension refluxed for 20 min
  2. customThe cool reaction mixture
  3. additionwas poured into ice
  4. filtrationfiltered
  5. washwashed with water
  6. customrecrystallized from 2-propanol-water

Sources & evidence

ORD record
ord-02d8b51672894bb98c211573b685b277
Source dataset
uspto-grants-2005_06
Patent number
US06903114B2

Reaction notes

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