3-Aminophenol → 3-ethoxymethoxyphenylamine

HRID 1792732Notes

Reaction equation

HRID 1792732 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][CH2:14]Cl)[CH3:12]>C(#N)C>[CH2:11]([O:13][CH2:14][O:10][C:6]1[CH:5]=[C:4]([NH2:3])[CH:9]=[CH:8][CH:7]=1)[CH3:12]

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride

Product 1

HCID 120677493-ethoxymethoxyphenylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A dispersion of 12 g (274.9 mmol) of sodium hydride (55% in oil) was added portionwise at 0° C. to a solution of 20.0 g (183.3 mmol) of 3-aminophenol in 450 mL of dried acetonitrile. The mixture was then allowed to agitate at 0° C. for 3 hours. A solution of 25 g (210.8 mmol) of chloromethyl ethyl ether in 30 mL of acetonitrile was added dropwise, and the mixture was allowed to agitate overnight at room temperature. The reaction mixture was then filtered and the filter cake was washed with a small amount of acetone. The combined filtrates were evaporated. This gave 32.3 g of 3-ethoxymethoxyphenylamine. The resulting crude product was used in the next step without further purification.

Workup

  1. stirringto agitate overnight at room temperature
  2. filtrationThe reaction mixture was then filtered
  3. washthe filter cake was washed with a small amount of acetone
  4. customThe combined filtrates were evaporated
  5. customThe resulting crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-16738fd4d2a14dc786bb52e64ff9fd58
Source dataset
uspto-grants-2006_07
Patent number
US07077872B2

Reaction notes

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