Potassium Carbonate → 5-Chloro-2-(3-hydroxy-propoxy)-benzaldehyde

HRID 1728201

Reaction equation

HRID 1728201 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].Br[CH2:12][CH2:13][CH2:14][OH:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][CH2:13][CH2:14][OH:15])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 575659355-Chloro-2-(3-hydroxy-propoxy)-benzaldehydeYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-hydroxy-benzaldehyde (3.1 g, 20 mmol), 3-bromo-propan-1-ol (4.1 mL, 24 mmol), K2CO3 (5.5 g, 4 mmol) and KI (0.5 g) were mixed in DMF (20 mL). Then the mixture was irradiated under microwave at 200° C. for 1 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was separated, dried over Na2SO4 and concentrated to give title compound (Yield: 1.7 g, 59%).

Workup

  1. customThen the mixture was irradiated under microwave at 200° C. for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N NaOH
  6. customThen the organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-653dbb65be664e1fbbcc871c9d5ff7d6
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Linked notes

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