2-Phenylbutyric Acid → HCID 53887073, compound

HRID 249542Notes

Reaction equation

HRID 249542 reaction equation
[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:28][S:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1>C(Cl)Cl>[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([O:10][C:33]2[CH:34]=[CH:35][C:30]([S:29][CH3:28])=[CH:31][CH:32]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 140864-(Methylthio)phenol

Product 1

HCID 53887073HCID 53887073, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 2-phenylbutyric acid (4.93 g, 30 mmol) in 40 mL of CH2Cl2 at 0° C. was added dicyclohexylcarbodiimide (6.19 g, 30 mmol) in 30 mL of CH2Cl2. Solid 4-methylmercaptophenol (4.21 g, 30 mmol) was added and the suspension stirred at room temperature overnight. The precipitated urea was filtered, the filtrate evaporated and the residue chromatographed on silica gel (CH2Cl2)to give 4-(methylmercapto)phenyl 2-phenylbutyrate (6.23 g, 73%) as a light yellow oil which was crystallized from EtOH to give white crystals (mp 28.0°-28.5° C.). 1H NMR (CDCl3) δ0.98 (t, 3H, J=7.3 Hz), 1.89 (m, 1H), 2.22 (m, 1H), 3.68 (t, 1H, J=7.6 Hz), 6.92 (d, 2H, J=8.6 Hz), 7.22 (d, 2H, J= 8.6 Hz), 7.30-7.45 (m, 5H, ArH).

Workup

  1. filtrationThe precipitated urea was filtered
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica gel (CH2Cl2)to

Sources & evidence

ORD record
ord-ea45a3d86b984a4e90d5137872ad3e99
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Reaction notes

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