Chlorotrimethylsilane → Methyl 2-(3-methoxyphenyl)acetate

HRID 722359Notes

Reaction equation

HRID 722359 reaction equation
[CH3:1][Si](Cl)(C)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=1>CO>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]([O:17][CH3:1])=[O:16])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 519609Methyl 2-(3-methoxyphenyl)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl chloride (182 g, 1.68 mol) was added dropwise to a solution of 3-methoxyphenylacetic acid (127 g, 0.77 mol) in methanol (1.0 L) over 1.1 hours. The reaction was stirred at room temperature for 17.25 hours, concentrated in vacuo, dissolved in ethyl acetate, dried over MgSO4, and concentrated in vacuo, to give a brown oil (133 g, 97%): 1H NMR (CDCl3/300 MHz) 7.24 (t, 1H, J=7.5 Hz), 6.83 (m, 3H), 3.80 (s, 3H), 3.69 (s, 3H), 3.60 (s, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026a3eb1061c423bbfb662a91de1074a
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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