2-Isopropylphenol → 4-(2-Isopropyl-phenoxy)-benzaldehyde

HRID 2040110

Reaction equation

HRID 2040110 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 69432-IsopropylphenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 226841824-(2-Isopropyl-phenoxy)-benzaldehydeYield 77.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-fluoro-benzaldehyde (1.5 g, 12.08 mmol) and 2-isopropyl-phenol (1.64 g, 12.08 mmol) in anhydrous N,N-dimethyl acetamide (20 mL) was added granulated potassium carbonate (3.7 g, 26.58 mmol). The reaction mixture was stirred at 150° C. for 18 hours and was partitioned between ethyl acetate and brine. The ethyl acetate layer was washed with saturated aqueous hydrogenocarbonate solution, brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (15% ethyl acetate in n-heptane) to yield 4-(2-Isopropyl-phenoxy)-benzaldehyde as a gum (2.25 g, 77%).

Workup

  1. customwas partitioned between ethyl acetate and brine
  2. washThe ethyl acetate layer was washed with saturated aqueous hydrogenocarbonate solution, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude oil
  7. customThe crude oil was purified via flash chromatography (15% ethyl acetate in n-heptane)

Sources & evidence

ORD record
ord-ef1f5f9eb948457884b313fb138f8f37
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Linked notes

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