Methyl iodide → Methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate

HRID 371379Notes

Reaction equation

HRID 371379 reaction equation
[C:1]([O:14][CH3:15])(=[O:13])[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[H-].[K+].[CH3:18]I>O1CCCC1>[CH3:18][CH:2]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[C:1]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 10536335Benzeneacetic acid, 4-(methoxycarbonyl)-, methyl ester

Product 1

HCID 157136Methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoateYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dimethyl homoterephthalate (4.16 g, 20 mmoles) in 15 ml of dry tetrahydrofuran was added dropwise over 15 min to a stirred mixture of potassium hydride (2.5 g of 35% oil suspension, 22 mmole) in 75 ml of dry tetrahydrofuran at 0° C. After 30 min a homogeneous yellow suspension had formed. Methyl iodide (2.79 g, 22 mmole) was then added over a 5 minute period and the resulting mixture stirred for 30 minutes. The mixture was quenched with 2 ml of 50% acetic acid, diluted with 500 ml of water and extracted with ether. The ether extract was washed with water, dried over magnesium sulfate and evaporated to leave an oil. The material was chromatographed on silica gel with elution by ether-hexane (1:9) to afford (71%) of a clear oil; m/e 222 (M+): NMR (CDCl3) 1.50 (3H, d, CH3), 3.65 (3 H, s, OCH3), 3.93 (3H, s, OCH3 benzoate).

Workup

  1. customAfter 30 min a homogeneous yellow suspension had formed
  2. customThe mixture was quenched with 2 ml of 50% acetic acid
  3. additiondiluted with 500 ml of water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto leave an oil
  10. customThe material was chromatographed on silica gel with elution by ether-hexane (1:9)

Sources & evidence

ORD record
ord-f3b0c18c58c9462290f5ed577d9cf706
Source dataset
uspto-grants-1985_07
Patent number
US04532241

Reaction notes

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