2-Aminophenol → HCID 66726640, compound

HRID 2364945Notes

Reaction equation

HRID 2364945 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]1[O:19][C:12]2([CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[O:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C(Cl)Cl>[O:11]1[C:12]2([CH2:17][CH2:16][CH:15]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[OH:8])[CH2:14][CH2:13]2)[O:19][CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 58012-AminophenolHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66726640HCID 66726640, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-aminophenol (2 g, 18.327 mmol), 1,4-cyclohexanedione monoethyleneketal (3.721 g, 23.825 mmol), and sodium triacetoxy-borohydride (5.826 g, 27.491 mmol) in DCE (20 ml) and acetic acid (0.2 ml) was stirred at r.t. for 3 h. The r.m. was diluted with DCM and washed with NaHCO3 aqueous saturated solution, dried (Na2SO4) and the solvent was evaporated in vacuo. The solid residue thus obtained was triturated with diisopropyl ether to yield D8 (3.78 g) as a white solid.

Workup

  1. washwashed with NaHCO3 aqueous saturated solution
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe solid residue thus obtained
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-2082494a79c340b493976f914975c7be
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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