Sodium Hydroxide → 2-(4-Aminophenyl)-2-methylpropan-1-ol

HRID 2404809Notes

Reaction equation

HRID 2404809 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])([CH3:14])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15544083Ethyl 2-(4-aminophenyl)-2-methylpropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 219047282-(4-Aminophenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-(4-aminophenyl)-2-methylpropanoate (30 mg, 0.145 mmol) in THF (1 mL) was treated with LiAlH4 (1M solution in THF, 0.226 mL, 0.226 mmol) at 0° C. and stirred for 15 min. The reaction was treated with 0.1N NaOH, extracted with EtOAc and the organic layers were dried over Na2SO4. The solvent was removed under reduced pressure to yield 2-(4-aminophenyl)-2-methylpropan-1-ol (G-2), which was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8.5 Hz, 2H), 6.67 (d, J=8.5 Hz, 2H), 3.53 (s, 2H), 1.28 (s, 6H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe organic layers were dried over Na2SO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-379b083d40794844a027a31d6fdb10f8
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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