2-Phenylbutyric Acid → 1-(4-(4-Chlorobutoxy)phenyl)-2-phenyl-1-butanone

HRID 1082138Notes

Reaction equation

HRID 1082138 reaction equation
[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=O)(O)[O-].[Na+]>[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:8](=[O:10])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][CH3:12])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 70122-Phenylbutyric AcidHCID 758574-Chlorobutyl phenyl ether

Product 1

HCID 99739431-(4-(4-Chlorobutoxy)phenyl)-2-phenyl-1-butanoneYield 94.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2-phenylbutyric acid (5.6 g, 34 mmol) in trifluoroacetic anhydrlde (20 ml) was added 4-chlorobutoxybenzene (7.5 g, 41 mmol). After 16 h, the mixture was poured into saturated sodium bicarbonate solution (250 ml), and extracted with ether (2×100 ml). The combined organic layers were dried (MgSO4), and concentrated in vacuo. The residues were purified by flash chromatography (silica; eluant:10-30% ethyl acetate in petrol) to give the title compound as an orange oil (10.6 g, 94% ).

Workup

  1. extractionextracted with ether (2×100 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residues were purified by flash chromatography (silica; eluant:10-30% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-51124765cfec4fa780254dd993956a01
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

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