Methanol → Methyl bis(p-chlorophenyl)acetate

HRID 45552Notes

Reaction equation

HRID 45552 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:19]O>Cl>[CH3:19][O:10][C:9](=[O:11])[CH:8]([C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 6730Bis(4-chlorophenyl)acetic acid

Product 1

HCID 346996Methyl bis(p-chlorophenyl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

Bis-(4-chloro-phenyl)-acetic acid (4.33 g, 15.4 mmol) was suspended in anhydrous methanol (20 mL) and concentrated hydrochloric acid (5 drops) was added. After 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution, then the organic solvent was removed in vacuo. The residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give a residue which was purified by column chromatography (SiO2), eluting with 10% ethyl acetate/petrol, to afford the title compound as a colourless oil (3.57 g, 78%); LCMS (PS-B3) Rt 3.79 min, No ionisation. 1H NMR (CDCl3) δ 3.74 (3H, s), 4.96 (1H, s), 7.20-7.23 (4H, m), 7.28-7.32 (4H, m).

Workup

  1. customAfter 1 day the reaction was quenched by the addition of saturated sodium bicarbonate solution
  2. customthe organic solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and 50% saturated potassium carbonate solution
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified by column chromatography (SiO2)
  10. washeluting with 10% ethyl acetate/petrol

Sources & evidence

ORD record
ord-7a0a9537c79f43ebbb95dbd2d5cafed6
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

Loading…