2-Phenylbutyric Acid → HCID 10381092, compound

HRID 1082136Notes

Reaction equation

HRID 1082136 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1([CH:18]([CH2:22][CH3:23])[C:19](O)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(=O)(O)[O-].[Na+]>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:19](=[O:20])[CH:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][CH3:23])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 9845Trifluoroacetic anhydrideHCID 76917(3-Chloropropoxy)benzene

Product 1

HCID 10381092HCID 10381092, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent2×

Procedure

3-Chloropropoxybenzene (8g, 47 mmol) was added to a stirred solution of 2-phenylbutyric acid (8.5 g, 52 mmol) in trifluoroacetic anhydride (7.5 ml, 52 mmol) and stirring continued for 16 h. The mixture was poured into saturated sodium bicarbonate solution (100 ml), neutralized by addition of sodium bicarbonate, and extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (2×50 ml), dried (MgSO4), and concentrated in vacuo. The residues were distilled to give the title compound as a white waxy solid (12.01 g, 81%) bp 200° C. at 0.1 mm Hg.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic extracts were washed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. distillationThe residues were distilled

Sources & evidence

ORD record
ord-894d6e538a18471e839597a20059ce34
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

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