4-Hydroxybenzaldehyde → 4-Butoxybenzaldehyde

HRID 640258Notes

Reaction equation

HRID 640258 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 798134-ButoxybenzaldehydeYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). 1-Bromobutane (3.17 mL, 29.5 mmol) was added to this suspension, and stirred for 17 hours at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.72 g).

Workup

  1. customThe mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-7ba926d5a29b4ce69e2aa95f2a5373b8
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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