2-Phenylbutyric Acid → HCID 10548239, compound

HRID 1082141Notes

Reaction equation

HRID 1082141 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1([CH:23]([CH2:27][CH3:28])[C:24](O)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:24](=[O:25])[CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:27][CH3:28])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 9845Trifluoroacetic anhydrideHCID 10800118HCID 10800118, compound

Product 1

HCID 10548239HCID 10548239, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent2×

Procedure

8-Chlorooctoxybenzene (9.1 g, 38 mmol) was added to a stirred solution of 2-phenylbutyric acid (7.48 g, 46 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), neutralised by addition of sodium bicarbonate, and extracted with ether (2×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residues were column-chromatographed (silica; eluant 5-10% dichloromethane in petrol) to give the title compound as a colourless oil (11.86 g, 81%). NMR (CDCl3) δ=0.87 (3H,t,J=7.3 Hz), 1.26-1.50 (8H, m), 1.69-1.90 (5H,m), 2.08-2.26 (1H,m), 3.51 (2H,t,J=6.6 Hz), 3.94 (2H,t,J=6.6 Hz), 4.38 (1H,t,J=7.3 Hz), 6.83 (2H,d,J=8.8 Hz), 7.15-7.20 (1H,m), 7.20-7.28 (4H,m), 7.93 (2H,d,J=8.8 Hz). IR (liq, cm-1) 2933, 2858, 1673, 1600, 1574, 1510 MS(Chemical Ionisation)m/e=387 (M+ +1, 10%)

Workup

  1. extractionextracted with ether (2×100 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residues were column-chromatographed (silica; eluant 5-10% dichloromethane in petrol)

Sources & evidence

ORD record
ord-902d48c1503445d9980e8f7d641a46a6
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

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