Water → 2,6-Di-tert-butyl-4-vinylphenol

HRID 1801421Notes

Reaction equation

HRID 1801421 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])[CH:8]=[CH:9]C(O)=O)([CH3:4])([CH3:3])[CH3:2].O>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH2:9])[CH:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid

Product 1

HCID 125766802,6-Di-tert-butyl-4-vinylphenolYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-di-tert-butyl-4-hydroxycinnamic acid (2.77 g, 10 mmol) in dry DMF (20 mL) was refluxed at 150° C. under N2 for 2 h with stirring. The resulting mixture was then poured into water (200 mL) and extracted with chloroform (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with hexane, to give 2.094 g (90.2%) of the title compound as a colorless solid: mp 51-51.5° C.; 1H NMR (400 MHz, CDCl3): δ 7.248 (s, 2H), 6.666 (d×d, 1H, J=10.8 Hz, J2=17.6 Hz), 5.587 (d, 1H, J=16.8 Hz), 5.241 (s, 1H), 5.094 (d, 1H, J=10.8 Hz), 1.456 (s, 18H); 13C NMR (100 MHz, CDCl3): δ 153.980, 137.529, 136.055, 129.040, 123.216, 110.996, 34.565, 30.507; Anal. Calcd. for C16H24O: C, 82.70; H, 10.41. Found; C, 83.08; H, 10.37.

Workup

  1. extractionextracted with chloroform (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-b670e37f79c947cd8bd27ea36bd97949
Source dataset
uspto-grants-2013_01
Patent number
US08349222B2

Reaction notes

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