4-Hydroxybenzaldehyde → 4-(3,3,3-Trifluoropropoxy)benzaldehyde

HRID 339510Notes

Reaction equation

HRID 339510 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:10][C:11]([F:16])([F:15])[CH2:12][CH2:13][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 11776TriphenylphosphineHCID 1375123,3,3-Trifluoro-1-propanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 583421884-(3,3,3-Trifluoropropoxy)benzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-hydroxybenzaldehyde (0.36 g, 2.93 mmol), 3,3,3-trifluoropropanol (0.5 g, 4.39 mmol) and triphenylphosphine (1.15 g, 4.39 mmol) in dry THF (10 ml) at 0° C. under an atmosphere of argon was added dropwise diisopropylazodicarboxylate (0.89 g, 4.39 mmol). On completion of the addition, the reaction mixture was stirred at room temperature for 60 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (4:1 Hexane/EtOAc) to give the title compound (0.25 g, 46%) as a colourless solid.

Workup

  1. additionOn completion of the addition
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (4:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-30640eb58511495b83faa2a0fcf20d35
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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