4-Hydroxybenzaldehyde → 4-(2-Chloroethoxy)benzaldehyde

HRID 896480Notes

Reaction equation

HRID 896480 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][Cl:19].[OH-].[Na+]>CN(C)C=O.O>[Cl:19][CH2:18][CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 1431564-(2-Chloroethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 4-hydroxybenzaldehyde (0.082 mol) in dimethylformamide (100 ml) and add potassium carbonate (0.164 mol) and 1-bromo-2-chloroethane (0.246 mol). Stir magnetically for five days at ambient temperature, then hydrolyse the reaction mixture in 500 ml of water and render alkaline with 3 g of sodium hydroxide pellets. Extract twice with 50 ml of ether each time. Dry the organic phase over magnesium sulphate and remove the ether by evaporation under reduced pressure. Purify the resulting oil by flash chromatography using a 9/1 cyclohexane/ether mixture as eluant. Subsequently, remove the mixture of solvents by evaporation under reduced pressure and crystallise the resulting yellow oil and store it in a dessicator.

Workup

  1. extractionExtract twice with 50 ml of ether each time
  2. dry with materialDry the organic phase over magnesium sulphate
  3. customremove the ether
  4. customby evaporation under reduced pressure
  5. customPurify the resulting oil by flash chromatography
  6. customSubsequently, remove
  7. additionthe mixture of solvents
  8. customby evaporation under reduced pressure
  9. customcrystallise the resulting yellow oil and store it in a dessicator

Sources & evidence

ORD record
ord-9397a16386a74d0fbbdd1942682e041c
Source dataset
uspto-grants-2005_07
Patent number
US06919362B2

Reaction notes

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