Methyl iodide → Methyl 2-(4-hydroxyphenyl)propanoate

HRID 1164774Notes

Reaction equation

HRID 1164774 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.[CH3:17]I>C(COC)OC>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 601552Methyl {4-[(trimethylsilyl)oxy]phenyl}acetate

Product 1

HCID 12549710Methyl 2-(4-hydroxyphenyl)propanoateYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of methyl 2-(4'-trimethylsilyloxyphenyl)ethanoate (34.3 mmole) in dimethoxyethane (10 ml) was added dropwise to the reaction, the temperature rising to -30° C. before cooling to -70° C. This cold reaction mix was added dropwise to a solution of methyliodide (0.16 mole) in dimethoxyethane (20 ml) cooled to -70° C. The mixture was stirred at room temperature overnight before removing the solvent by evaporation. The residue was stirred with dilute HCl and extracted with dichloromethane, washed with saturated NaHCO3 solution, dried (MgSO4) and the product isolated by evaporation. Distillation of the crude product gave MHPP (yield 88%).

Workup

  1. customrising to -30° C.
  2. customThis cold reaction
  3. additionmix
  4. temperaturecooled to -70° C
  5. custombefore removing the solvent
  6. customby evaporation
  7. stirringThe residue was stirred with dilute HCl
  8. extractionextracted with dichloromethane
  9. washwashed with saturated NaHCO3 solution
  10. dry with materialdried (MgSO4)
  11. customthe product isolated by evaporation
  12. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-a210697945604896a8c3f4a5f8e7cdf3
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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