Resorcinol → 3-(propan-2-yloxy)phenol

HRID 222643Notes

Reaction equation

HRID 222643 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.I[CH:10]([CH3:12])[CH3:11].[OH-].[K+].[OH-].[Na+]>C(O)C.O>[CH:10]([O:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1)([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 14798Sodium Hydroxide

Product 1

HCID 2353733-(propan-2-yloxy)phenolYield 43%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-hydroxyphenol (20.0 g, 0.182 mmoL), 2-iodopropane (30.9 g, 0.182 mmoL) in ethanol (25 mL) at refluxing was added KOH (88%, 12.2 g, 0.191 mmoL) in water (30 mL) over a period of 60 min. The resulting mixture was refluxed for 3 hours. The mixture was poured into 1N NaOH and extracted with ether (1×). The aqueous layer was acidified with 10% HCl to pH 5 and extracted with ether (2×). The combined extracts were washed with brine (1×), dried over MgSO4 and concentrated. The residue was purified on silica gel eluting with ethyl acetate:hexane (1:8) to give the desired product as a colorless liquid (11.7 g, 43%). This was used directly in the next step. 1H NMR (500 MHz, CDCl3) δ ppm 7.10 (t, 1H) 6.47 (d, J=7.32 Hz, 1H) 6.36-6.42 (m, 1H) 4.70 (s, 1H) 4.45-4.55 (m, 1H) 4.13 (q, J=7.32 Hz, 1H) 1.32 (d, 6H). MS m/z (DCI) 153.0 (M+H)+.

Workup

  1. temperatureat refluxing
  2. temperatureThe resulting mixture was refluxed for 3 hours
  3. extractionextracted with ether (1×)
  4. extractionextracted with ether (2×)
  5. washThe combined extracts were washed with brine (1×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel eluting with ethyl acetate:hexane (1:8)

Sources & evidence

ORD record
ord-89106c3715754ddfac00b331a311958f
Source dataset
uspto-grants-2012_06
Patent number
US08207350B2

Reaction notes

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