Acetyl chloride → Methyl 3,5-dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetate

HRID 2108630Notes

Reaction equation

HRID 2108630 reaction equation
[C:1](Cl)(=O)C.[CH3:5][C:6]1[CH:7]=[C:8]([CH2:25][C:26]([OH:28])=[O:27])[CH:9]=[C:10]([CH3:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1>CO>[CH3:5][C:6]1[CH:7]=[C:8]([CH2:25][C:26]([O:28][CH3:1])=[O:27])[CH:9]=[C:10]([CH3:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 666426363,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetic acid

Product 1

HCID 66642908Methyl 3,5-dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred cold solution of methanol (15 mL) and acetyl chloride (3 mL, 86.0 mmol) at 0° C. was added dropwise a solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenylacetic acid (0.7 g, 4.3 mmol) in methanol (5 mL). The reaction mixture was heated under reflux for 5 h and cooled to room temperature. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL). The organic solution was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was triturated with hexane, filtered and dried under reduced pressure to afford methyl 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenylacetate as a yellow solid (0.69 g, 95%): 1H NMR (300 MHz, CDCl3): δ 7.02 (s, 2 H), 6.82 (d, J=2.7 Hz, 1 H), 6.66 (d, J=8.7 Hz, 1 H), 6.38 (dd, J=3.3, 8.7 Hz, 1 H), 3.79 (s, 3 H), 3.75 (s, 3 H), 3.60 (s, 2 H), 3.28-3.25 (m, 1 H), 2.14 (s, 6 H), 1.20 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:1); Rf=0.6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was triturated with hexane
  10. filtrationfiltered
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-54f10955b72c4a119047ff781e1d7fa7
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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