3-Aminophenol → 3-(Cyclopropylmethoxy)benzenamine

HRID 2274925Notes

Reaction equation

HRID 2274925 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH:9]1([CH2:12]O)[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:9]1([CH2:12][O:8][C:4]2[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 115683-AminophenolHCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 289582373-(Cyclopropylmethoxy)benzenamineYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-aminophenol (300 mg, 2.70 mmol), cyclopropylmethanol (793 mg, 11.0 mmol) and triphenylphosphine (2.90 g, 11.0 mmol) in THF (6 mL) was added dropwise diethylazodicarboxylate (1.90 g, 11.0 mmol) over a 30 min period. The mixture was stirred at room temperature for 3 h. The solvent was evaporated and the residue was diluted with water, acidified with aqueous 2N HCl and extracted with ether. The aqueous phase was basified with aqueous 2N NaOH and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated. The resulting crude product was purified by silica gel column chromatograph (petroleum ether/EtOAc 15:1) to afford 3-(cyclopropylmethoxy)benzenamine as a brown oil (260 mg, 58%).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatograph (petroleum ether/EtOAc 15:1)

Sources & evidence

ORD record
ord-52936bce535d4dcd8905387f992eb700
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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