3-Hydroxybenzaldehyde → 3-butoxybenzaldehyde

HRID 640250Notes

Reaction equation

HRID 640250 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].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:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 27572023-butoxybenzaldehydeYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-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 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. This 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 (4.23 g).

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThis 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-e963e5f528ab4cb2947a83b903068f2d
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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