Iodoethane → 4-(Diethylamino)-2-ethoxybenzaldehyde

HRID 1597877

Reaction equation

HRID 1597877 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:21](I)[CH3:22]>CN(C=O)C>[CH2:21]([O:1][C:2]1[CH:9]=[C:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 9587084-(Diethylamino)-2-ethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-hydroxy-4-(diethylamino)benzaldehyde (10.0 g, 51.75 mmol), K2CO3 (14.3 g) and DMF (150 ml) at room temperature was added ethyl iodide (4.1 ml). The reaction mixture was stirred for about two days, filtered and the filtrate was concentrated in vacuo. The residue was partitioned between ether and saturated Na2CO3, and the organic layer was separated, dried over MgSO4, treated with charcoal, filtered and concentrated in vacuo. The solid product was recrystallized from hexane to afford, as a pink crystalline solid, 9.8 g of 2-ethoxy-4-(diethylamino)benzaldehyde, m.p. 58°-59° C.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between ether and saturated Na2CO3
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid product was recrystallized from hexane

Sources & evidence

ORD record
ord-74f2fdcf110243d69e31a6aaf65fef76
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Linked notes

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