Iodoethane → 2-Ethoxynaphthalene-1-carbaldehyde

HRID 434865

Reaction equation

HRID 434865 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13].I[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 128192-Hydroxy-1-naphthaldehyde

Product 1

HCID 880992-Ethoxynaphthalene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Hydroxy-1-naphthaldehyde (10 g., 0.058 mole) was combined with acetone (120 ml.), iodoethane (9.9 g., 0.063 mole) and anhydrous potassium carbonate (8.0 g., 0.058 mole) and the mixture heated to reflux for 48 hours. The reaction mixture was cooled to room temperature, filtered and filtrate evaporated to solids (9.0 g.) Recrystallization from isopropyl ether afforded purified 2-ethoxy-1-naphthaldehyde in two crops (4.5 g. and 0.5 g., m.p. 106°-109° C.).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. customfiltrate evaporated to solids (9.0 g.) Recrystallization from isopropyl ether
  5. customafforded
  6. custompurified 2-ethoxy-1-naphthaldehyde in two crops (4.5 g. and 0.5 g., m.p. 106°-109° C.)

Sources & evidence

ORD record
ord-20890d9abb4f4ab7bf17d96c6437c002
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Linked notes

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