Pyridine → 4-methylphenyl 3-chloropropanoate

HRID 2120119Notes

Reaction equation

HRID 2120119 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].[CH:7]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]([CH3:14])[CH:8]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][C:4]([O:13][C:12]1[CH:11]=[CH:10][C:9]([CH3:14])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2879P-CresolHCID 693643-Chloropropionyl chloride

Product 1

HCID 41030644-methylphenyl 3-chloropropanoateYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloropropionyl chloride (12.5 ml, 0.131 mol) was added for three minutes to a solution of p-cresol (12.90 g, 0.119 mol) in pyridine (9.5 ml, 0.12 mol) and CH2Cl2 (53 ml) at 0° C. After stirring the reaction mixture for one day at 0° C. to room temperature, solvent was removed by rotary evaporation. The concentrate was treated with brine (50 ml) and 0.5 M citric acid (150 ml) and extracted with EtOAc (3×100 ml). The organic extracts were washed with 100 ml; 1 N HCl, H2O, cold 0.1 N NaOH, H2O and brine. After solvent removal, the residue was purified by silica gel flash column chromatography eluting with 7.5% EtOAc/hexane to give 12.90 g (55%) of 19 as a colorless liquid: NMR δ 2.34 (s, 3H), 3.03 (t, 2H, J=7), 3.86 (t, 2H, J=7), 6.95-7.01 (m, 2H), 7.17 (d, 2H, J=8).

Workup

  1. customsolvent was removed by rotary evaporation
  2. additionThe concentrate was treated with brine (50 ml) and 0.5 M citric acid (150 ml)
  3. extractionextracted with EtOAc (3×100 ml)
  4. washThe organic extracts were washed with 100 ml
  5. customAfter solvent removal
  6. customthe residue was purified by silica gel flash column chromatography
  7. washeluting with 7.5% EtOAc/hexane

Sources & evidence

ORD record
ord-fc64a88ba477400e80e40878fa31505e
Source dataset
uspto-grants-2004_02
Patent number
US06689788B1

Reaction notes

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