Hydrochloric Acid → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenol

HRID 2108625Notes

Reaction equation

HRID 2108625 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)C=O.ClC1C=C(C=CC=1)C(OO)=[O:28].[OH-].[Na+].Cl>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([OH:28])[CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 222856654-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-benzaldehyde

Product 1

HCID 251504203,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenolYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzaldehyde (0.18 g, 0.60 mmol, Example 28, step a) in dichloromethane (6.0 mL) at 0° C. was added m-chloroperoxybenzoic acid (0.22 g, 0.905 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the residue was diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate (2×10 mL) and water. The solvent was removed under reduced pressure and the residue was dissolved in methanol (5 mL). To the solution was added 1 N NaOH (1.81 mL, 1.81 mmol) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate, acidified with 2 N HCl and washed with brine. The solvent was evaporated and the residue was purified by preparatory TLC eluting with acetone-hexanes (1:4) to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenol as an oil (0.08 g, 47%): 1H NMR (200 MHz, DMSO-d6): δ 9.17 (s, 1 H), 6.82 (m, 1 H), 6.70 (m, 1 H), 6.51 (s, 2 H), 6.32 (m, 1 H), 3.71 (s, 3 H), 3.18 (m, 1 H), 1.95 (s, 6 H), 1.12 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (4:1); Rf=0.44.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate (2×10 mL) and water
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (5 mL)
  6. stirringthe reaction mixture was stirred at room temperature for 4 h
  7. washwashed with brine
  8. customThe solvent was evaporated
  9. customthe residue was purified by preparatory TLC
  10. washeluting with acetone-hexanes (1:4)

Sources & evidence

ORD record
ord-b109efce876e4277ba7f24ada2dd9aa0
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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