6-Methoxy-2-naphthaldehyde → 6-Hydroxy-2-naphthaldehyde

HRID 898188

Reaction equation

HRID 898188 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=[O:18])[CH:11]=[CH:10]2>ClC1C=CC=CC=1>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=[O:18])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 769916-Methoxy-2-naphthaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27641106-Hydroxy-2-naphthaldehydeYield 37.9%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
130 °C

Procedure

Aluminum trichloride (1.07 g, 8.06 mmol) was added to a solution of 6-methoxy-2-naphthaldehyde (1.0 g, 5.37 mmol) in chlorobenzene (15 mL). The reaction mixture was stirred at 130° C. for 4 h. The reaction was quenched with water (5 mL) and conc. HCl (2 mL). The reaction mixture was dissolved in ethyl acetate and washed with water and brine and dried over anhydrous magnesium sulfate. Silica gel chromatography eluting with 10% ethyl acetate/hexane yielded 0.35 g of desired product: ESI-MS173.0 (M+H).

Workup

  1. customThe reaction was quenched with water (5 mL) and conc. HCl (2 mL)
  2. dissolutionThe reaction mixture was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washSilica gel chromatography eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-89c00d81e8fb4583825a73f1263c7bee
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Linked notes

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