Acetone → 2-Methoxy-1-naphthaldehyde

HRID 654591Notes

Reaction equation

HRID 654591 reaction equation
BrC(Br)[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.O.C[C:18](C)=[O:19]>>[CH3:14][O:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:3][CH:4]=2)[C:9]=1[CH:18]=[O:19]

Participants

4

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 10958469HCID 10958469, compound

Product 1

HCID 793522-Methoxy-1-naphthaldehyde

Conditions

Temperature
24 °C

Procedure

A solution of 2-dibromomethyl-6-methoxynaphthalene (3 g) in acetone (25 ml) was treated with water (7 ml) and the mixture stirred at 24° C. for 10 hours. The solvent was removed under vacuum and the residue dissolved in toluene (30 ml). The toluene solution was washed with saturated sodium bicarbonate solution (2×10 ml) and water (10 ml) and dried over MgSO4. The dried solution was filtered and the filtrate evaporated down to a yellowish-brown semi-solid. This was recrystallised twice from isopropanol (2×10 ml) to give 0.5 g of pure 2-methoxynaphthaldehyde as confirmed using HPLC (conditions; spheresorb C18 25 cm×4.5 mm i.d. (column), 65% acetonitrile/35% water (eluent), 1 ml/min (flowrate), 310 nm (wavelength). The samples were dissolved in acetonitrile and 20 μl injected onto the column. The retention time for 2-methoxynaphthaldehyde was about 6 minutes.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in toluene (30 ml)
  3. washThe toluene solution was washed with saturated sodium bicarbonate solution (2×10 ml) and water (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationThe dried solution was filtered
  6. customthe filtrate evaporated down to a yellowish-brown semi-solid
  7. customThis was recrystallised twice from isopropanol (2×10 ml)

Sources & evidence

ORD record
ord-7f40f6d3141e4ae6b8d80eca92a75df8
Source dataset
uspto-grants-1992_07
Patent number
US05132466

Reaction notes

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