3-Hydroxybenzaldehyde → 3-(3,3,3-Trifluoropropoxy)benzaldehyde

HRID 1371898Notes

Reaction equation

HRID 1371898 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].S(C1C=CC(C)=CC=1)(OO[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:18][C:17]([F:20])([F:19])[CH2:16][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 210715103,3,3-Trifluoropropoxy tosylate

Product 1

HCID 210715093-(3,3,3-Trifluoropropoxy)benzaldehydeYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 3-hydroxybenzaldehyde (130.2 g, 1.066 mol), 3,3,3-trifluoropropoxy tosylate (143 g, 0.533 mol), potassium carbonate (147.35 g, 1,066 mol) and absolute ethanol (1430 mL) in a three-necked round-bottomed flask equipped with a reflux condenser and a magnetic stirred and reflux for 4 h under argon atmosphere. Concentrate the reaction mixture under reduced pressure. Pour the concentrated mixture over 1N sodium hydroxide (2145 mL), stir for 30 min and extract with dichloromethane (2145 mL). Decant the organic layer wash with 1N sodium hydroxide (2145 mL). After separation, wash the organic layer successively twice by 1 L water (pH aqueous phase=7), dry over 30 g magnesium sulfate, evaporate the dichloromethane organic layer to dryness under reduced pressure to yield 55.4 g of the title compound (0.254 mol, 47.6% yield) as a slightly yellow oily material.

Workup

  1. temperaturereflux for 4 h under argon atmosphere
  2. concentrationConcentrate the reaction mixture under reduced pressure
  3. additionPour the concentrated mixture over 1N sodium hydroxide (2145 mL)
  4. stirringstir for 30 min
  5. extractionextract with dichloromethane (2145 mL)
  6. customDecant the organic layer
  7. washwash with 1N sodium hydroxide (2145 mL)
  8. customAfter separation
  9. washwash the organic layer successively twice by 1 L water (pH aqueous phase=7)
  10. dry with materialdry over 30 g magnesium sulfate
  11. customevaporate the dichloromethane organic layer to dryness under reduced pressure

Sources & evidence

ORD record
ord-d94f60cecb4c4cf5bdc1fa13d1f69f4a
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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