Trifluoroacetic acid → (+/-)-7-(4-Fluorophenoxy)-6-(hydroxy)-heptan-al

HRID 2304114Notes

Reaction equation

HRID 2304114 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH:8]([O:15]COCCOC)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 18533431(+/-)-7-(4-Fluorophenoxy)-6-(2-methoxyethoxymethoxy)-heptan-1-al

Product 1

HCID 23251246(+/-)-7-(4-Fluorophenoxy)-6-(hydroxy)-heptan-alYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(±)-7-(4-fluorophenoxy)-6-(2-methoxyethoxymethoxy)heptan-1-al 45 (2 g, 6.1 mmol) and 2 ml of trifluoroacetic acid are added to 10 ml of chloroform. The reaction mixture is stirred for 24 hours and then is neutralized with 1% aqueous NaOH. The organic layer is washed with water, brine, dried (Na2SO4), concentrated. The crude trifluoroacetyl-aldehyde 46 is then dissolved in MeOH:H2O (1:1) and solid K2CO3 is added to maintain pH 8. The reaction is complete is approximately 15 minutes, as monitored by TLC (ethyl acetate:hexane 3:7). Methanol is removed in vacuo and remaining solution is extracted with ethyl acetate to give (±)-7-(4-fluorophenoxy)-6-(hydroxy)-heptan-al 47 (1.2 g, 82%).

Workup

  1. washThe organic layer is washed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. dissolutionThe crude trifluoroacetyl-aldehyde 46 is then dissolved in MeOH:H2O (1:1)
  5. additionsolid K2CO3 is added
  6. temperatureto maintain pH 8
  7. waitThe reaction is complete is approximately 15 minutes
  8. customMethanol is removed in vacuo
  9. extractionis extracted with ethyl acetate

Sources & evidence

ORD record
ord-f351f095afad49669f715843ab64e091
Source dataset
uspto-grants-2002_08
Patent number
US06433197B1

Reaction notes

Loading…