Diethyl Ether → 2-(2-Amino-3-methylphenyl)propan-2-ol

HRID 1263173Notes

Reaction equation

HRID 1263173 reaction equation
[CH3:1]I.[Mg].[CH3:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:8](C(OC)=O)[C:6]=1[NH2:7].[Cl-].[NH4+].C([O:20][CH2:21][CH3:22])C>>[CH3:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([C:21]([OH:20])([CH3:22])[CH3:1])[C:6]=1[NH2:7]

Participants

6

Reactant 5

HCID 3283Diethyl Ether3×HCID 6328Methyl iodideHCID 25517Ammonium Chloride2×HCID 2763406Methyl 3-methylanthranilateHCID 5462224Magnesium

Product 1

HCID 139590002-(2-Amino-3-methylphenyl)propan-2-ol

Procedure

In this example a solution containing 381.46 g of methyl iodide in 500 ml of ethyl ether was added dropwise to 65.3 g of magnesium submerged in ethyl ether at room temperature and under nitrogen. The mixture was then cooled and then a solution containing 0.67 moles of 2-methyl-6-methoxycarbonylaniline in 500 ml of ethyl ether was dropwise added thereto. The mixture was then refluxed for 21/2 hours, then cooled and 750 ml of saturated aqueous ammonium chloride solution carefully added dropwise. Additional ammonium chloride solution was then added and the resulting mixture filtered through diatomaceous earth. The water layer in the filtrate was decanted from the ether layer and washed with ether. The ether washings were combined with the ether layers washed with water, dried and evaporated to dryness affording the title product.

Workup

  1. temperatureThe mixture was then cooled
  2. additionwas dropwise added
  3. temperatureThe mixture was then refluxed for 21/2 hours
  4. temperaturecooled
  5. filtrationthe resulting mixture filtered through diatomaceous earth
  6. customThe water layer in the filtrate was decanted from the ether layer
  7. washwashed with ether
  8. washwashed with water
  9. customdried
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-cbc12116e5044002868e4900a7a017cf
Source dataset
uspto-grants-1984_06
Patent number
US04456471

Reaction notes

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