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

HRID 1371936Notes

Reaction equation

HRID 1371936 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8])(=O)=O.[OH:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:8][C:7]([F:10])([F:9])[CH2:6][CH2:5][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonate

Product 1

HCID 210715093-(3,3,3-Trifluoropropoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 3,3,3-trifluoropropyl tosylate (4.057 gm; 15.12 mmol), 3-hydroxybenzaldehyde (1.85 gm; 15.12 mmol), and K2CO3 (4.15 gm; 30.0 mmol) in DMF (80 mL) and heat at 100° C. After 18 hours, cool to room temperature, dilute with water (200 mL) and extract with dichloromethane (2×200 mL). Combine organic extracts and wash sequentially with water (100 mL), 0.1 M NaOH (2×100 mL), saturated sodium bicarbonate (100 mL) and saturated brine (100 mL), dry (MgSO4), and concentrate. Chromatography on silica gel (0–20% ethyl acetate in hexane) to give the title product.

Workup

  1. extractionextract with dichloromethane (2×200 mL)
  2. washCombine organic extracts and wash sequentially with water (100 mL), 0.1 M NaOH (2×100 mL), saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-66a0cafb88d047e882c736265c39d73c
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

Loading…