Iodoethane → Methyl 3-ethoxy-4-methoxybenzoate

HRID 612051Notes

Reaction equation

HRID 612051 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:21]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium Carbonate2×HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 10536413Methyl 3-ethoxy-4-methoxybenzoateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 24.3 g (134 mmol) of methyl 3-hydroxy-4-methoxybenzoate, 36.8 g (267 mmol) of anhyd potassium carbonate and 31.4 g (201 mmol) of ethyl iodide in 500 mL of dimethylformamide was stirred at 100° C. for 5.5 h. An additional amount of ethyl iodide (31.4 g) and potassium carbonate (18.4 g) was added and heating was continued for 2 h more. The reaction was filtered and volatile material was removed from the filtrate in vacuo. The residue was slurried with water and filtered to collect the product which was washed with water and dried. Recrystallization from heptane gave 15.6 g of methyl 3-ethoxy-4-methoxybenzoate as white crystals: mass spectrum (electrospray, m/e): M+H 210.9.

Workup

  1. temperatureheating
  2. waitwas continued for 2 h
  3. filtrationThe reaction was filtered
  4. customvolatile material was removed from the filtrate in vacuo
  5. filtrationfiltered
  6. customto collect the product which
  7. washwas washed with water
  8. customdried
  9. customRecrystallization from heptane

Sources & evidence

ORD record
ord-c13c2ef738e34b6f9b1bd7364d376e0c
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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