Sulfuric Acid → 6-Hydroxy-2-naphthaldehyde

HRID 1360987Notes

Reaction equation

HRID 1360987 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2)#N.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].[OH:27]S(O)(=O)=O>CCCCCC.O>[OH:27][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 12433106HCID 12433106, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27641106-Hydroxy-2-naphthaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

6-Cyano-2-naphthalenecarbaldehyde (1.0 g, 5.9 mmol) was dissolved in dry hexane (15 mL) under nitrogen. The solution was cooled to −60° C. and a solution of diisobutyl aluminium hydride (DIBAH) (15 mL, 1M in hexane) was added dropwise. After the addition, the solution was left at room temperature overnight. Saturated ammonium chloride solution (20 mL) was added and the mixture was stirred at room temperature for 20 min, subsequently aqueous H2SO4 (10% solution, 15 mL) was added followed by water until all salt was dissolved. The resulting solution was extracted with ethyl acetate (3×), the combined organic phases were dried with MgSO4, evaporated to dryness to afford 0.89 g of 6-hydroxy-2-naphtalenecarbaldehyde.

Workup

  1. additionAfter the addition
  2. dissolutionwas dissolved
  3. extractionThe resulting solution was extracted with ethyl acetate (3×)
  4. dry with materialthe combined organic phases were dried with MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a93bed488ff54031b8e20079a942ac82
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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