Acetic Acid → 2-Methoxy-1-naphthaldehyde

HRID 974666Notes

Reaction equation

HRID 974666 reaction equation
BrC[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.C1N2CN3CN(C2)CN1C3.[C:25](O)(=[O:27])C.Cl>O>[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:25]=[O:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 100377832-bromomethyl-6-methoxynaphthalene

Product 1

HCID 793522-Methoxy-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromomethyl-6-methoxynaphthalene (12.68 g), hexamine (14 g), glacial acetic acid (21 ml) and water (21 ml) were heated under reflux with stirring for 30 minutes. Concentrated hydrochloric acid (16.6 ml) was then added and the mixture stirred and refluxed for a further 15 minutes. The reaction was cooled to room temperature and extracted with toluene (2×25 ml). The combined toluene extracts were washed with water (2×10 ml), saturated sodium bicarbonate solution (2×10 ml) and water (1×8 ml) and the toluene solution dried over MgSO4. The drying agent was filtered off and the solvent was removed by distillation under vacuum. This afforded 8.6 g of crude product which was recrystallised twice from isopropanol (2×50 ml) to give 6.07 g of 97.8% purity 2-methoxynaphthaldehyde as a light beige solid. The material had a melting point of 79.2° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux
  3. stirringthe mixture stirred
  4. temperaturerefluxed for a further 15 minutes
  5. extractionextracted with toluene (2×25 ml)
  6. washThe combined toluene extracts were washed with water (2×10 ml), saturated sodium bicarbonate solution (2×10 ml) and water (1×8 ml)
  7. dry with materialthe toluene solution dried over MgSO4
  8. filtrationThe drying agent was filtered off
  9. customthe solvent was removed by distillation under vacuum
  10. customThis afforded 8.6 g of crude product which was recrystallised twice from isopropanol (2×50 ml)

Sources & evidence

ORD record
ord-a39235b5a70a408aba909295ac7e273f
Source dataset
uspto-grants-1991_11
Patent number
US05068458

Reaction notes

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