Diethyl Ether → 2-(2-aminophenyl)propan-2-ol

HRID 437267Notes

Reaction equation

HRID 437267 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1C(OC)=O.[CH3:12][Mg]I.C([O:17][CH2:18][CH3:19])C>[Cl-].[NH4+]>[CH3:12][C:18]([OH:17])([CH3:19])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 8635Methyl AnthranilateHCID 178418373HCID 178418373, compound

Product 1

HCID 2535272-(2-aminophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A 30.2-g (0.2 mol) sample of methyl 2-aminobenzoate in 150 ml diethyl ether was added dropwise to a solution of methyl magnesium iodide (prepared from 19.4 g of Mg and 127.8 g of methyl iodide) in 150 ml diethyl ether. The reaction mixture was then heated under reflux for 1 hour, cooled, and diluted with 200 ml of saturated aqueous ammonium chloride solution. The resulting aqueous mixture was extracted with ether. The ether extracts were dried over magnesium sulfate and evaporated to give 19.1 g of α,α-dimethyl-2-aminobenzyl alcohol.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. extractionThe resulting aqueous mixture was extracted with ether
  5. dry with materialThe ether extracts were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-b239c5ceacbc4e17a689c95c775bb75c
Source dataset
uspto-grants-1977_06
Patent number
US04030906

Reaction notes

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