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

HRID 1583581Notes

Reaction equation

HRID 1583581 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][CH2:11][CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[F:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 129831-Chloro-2-fluoroethane

Product 1

HCID 150586494-(2-Fluoroethoxy)benzaldehydeYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxybenzaldehyde (26.0 g), 20.7 g of 1-fluoro-2-chloroethane and 42.4 g of anhydrous potassium carbonate were added to 100 ml of dimethylformamide, and reacted at 130° C. for 5 hours. After the reaction, the reaction mixture was cooled to room temperature, poured into water, and then extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure to give 35.6 g of crude 4-(2-fluoroethoxy)benzaldehyde.

Workup

  1. customreacted at 130° C. for 5 hours
  2. customAfter the reaction
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b5bd587e41f9426ca54f2eeb795b3b09
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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