Methanol → Methyl 2-(2-chloro-5-methoxyphenyl)acetate

HRID 1095947Notes

Reaction equation

HRID 1095947 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 153659582-Chloro-5-methoxybenzeneacetic acid

Product 1

HCID 15576550Methyl 2-(2-chloro-5-methoxyphenyl)acetate

Procedure

2-Chloro-5-methoxy-benzeneacetic acid (10 g, [CAS Reg. No. 91367-10-1]) was dissolved in MeOH (210 mL) and H2SO4 (0.7 mL) was added. The mixture was then refluxed overnight. Methanol was removed in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with sat. NaHCO3 and brine, dried over Na2SO4 and evaporated. The title compound was obtained as a light brown oil (10.16 g, 95%) and was used without further purification. 1H-NMR (δ, CDCl3): 7.27 (d, 1H), 6.83 (d, 1H), 6.77 (dd, 1H), 3.79 (s, 3H), 3.74 (s, 2H), 3.72 (s, 3H).

Workup

  1. temperatureThe mixture was then refluxed overnight
  2. customMethanol was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-8ecb174428a44ed4b05327d3f2a2ad24
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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