Acetic Acid → 2-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

HRID 1248091Notes

Reaction equation

HRID 1248091 reaction equation
CN(C)N=[C:4]([CH3:6])[CH3:5].[Li+].CCC[CH2-].[F:13][C:14]([F:34])([F:33])[C:15]1[CH:32]=[CH:31][C:18]([O:19][C:20]2[CH:30]=[CH:29][C:23]([O:24][CH:25]([CH3:28])[CH:26]=[O:27])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.C(O)(=[O:37])C>O1CCCC1>[OH:27][CH:26]([CH:25]([O:24][C:23]1[CH:29]=[CH:30][C:20]([O:19][C:18]2[CH:31]=[CH:32][C:15]([C:14]([F:33])([F:34])[F:13])=[CH:16][CH:17]=2)=[CH:21][CH:22]=1)[CH3:28])[CH2:5][C:4](=[O:37])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 61028n-Butyl lithiumHCID 1394772-Propanone, dimethylhydrazoneHCID 128567812-[4-(4-Trifluoromethylphenoxy)phenoxy]propanal

Product 1

HCID 202783992-Hexanone, 4-hydroxy-5-[4-[4-(trifluoromethyl)phenoxy]phenoxy]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of acetone N,N-dimethylhydrazone (0.32 g, 3.23 mmol) in tetrahydrofuran (THF; 5 ml) is added N-butyllithium (0.21 g, 3.23 mmol) at -65°, and the mixture is stirred for 30 minutes. To this is added dropwise 2-[4-(4-trifluoromethylphenoxy)phenoxy]propanal (1.0 g, 3.23 mmol) in 5 ml of THF, keeping the temperature at or below -60°. After 3 hours at -65°, the reaction mixture is allowed to warm to 0°, and is poured onto 20 g ice made slightly acidic with 10% acetic acid. It is extracted into ether, and the organic extract is washed with water and with NaCl and is dried over sodium sulfate. Solvent is removed, and the residue is purified by prep. TLC (silica gel, 20% ethyl acetate/hexane) to give 4-hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone (C'; Q1 is CH, Y is hydrogen, Z is trifluoromethyl, R 1 is methyl and R2 is methyl). ##STR21##

Workup

  1. custombelow -60°
  2. waitAfter 3 hours at -65°
  3. temperatureto warm to 0°
  4. extractionIt is extracted into ether
  5. extractionthe organic extract
  6. washis washed with water and with NaCl
  7. dry with materialis dried over sodium sulfate
  8. customSolvent is removed
  9. customthe residue is purified by prep

Sources & evidence

ORD record
ord-19c41b78be3d4096a4c254f1d8680c09
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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