Hydrochloric Acid → 2,3-Dihydroxy-1-naphthaldehyde

HRID 2185900Notes

Reaction equation

HRID 2185900 reaction equation
Cl.[OH:2][C:3]1[C:12]([OH:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C[CH2:15][O:16]CC>[C-]#N.[Zn+2].[C-]#N>[OH:2][C:3]1[C:12]([OH:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70912,3-Dihydroxynaphthalene

Product 1

HCID 133438102,3-Dihydroxy-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
60 °C

Procedure

A stream of HCl gas was passed through a stirred, cooled (0° C.) mixture of 2,3-dihydroxynaphthalene (6 g, 37.4 mmol) and zinc cyanide (6.6 g, 56.1 mmol) in dry Et2O (28 mL) for 20 min. An insoluble yellow oil was generated. Stirring was continued for 1 h at 0° C., then at room temperature for 1 h. The yellow brown oil was separated and washed with Et2O. Water (120 mL) was added and the mixture was heated at 60° C. for 10 min. The yellow solid generated was filtered and washed with water to give product (5.48 g, containing 20% starting material). MS (APCI) m/z 187 (M−H).

Workup

  1. temperaturecooled
  2. waitat room temperature for 1 h
  3. customThe yellow brown oil was separated
  4. washwashed with Et2O
  5. additionWater (120 mL) was added
  6. filtrationThe yellow solid generated was filtered
  7. washwashed with water
  8. customto give
  9. additionproduct (5.48 g, containing 20% starting material)

Sources & evidence

ORD record
ord-371eb2a8d2dd4c919f18e675dbb95d67
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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