Acrylic Acid → 6-hydroxy-5,7,8-trimethyl-chroman-2-one

HRID 2102984Notes

Reaction equation

HRID 2102984 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[C:12](O)(=[O:15])[CH:13]=[CH2:14]>CS(O)(=O)=O>[OH:11][C:3]1[C:2]([CH3:1])=[C:8]2[C:6](=[C:5]([CH3:9])[C:4]=1[CH3:10])[O:7][C:12](=[O:15])[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 12785Trimethylhydroquinone

Product 1

HCID 2973756-hydroxy-5,7,8-trimethyl-chroman-2-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of trimethyl-hydroquinone (3.04 g) and acrylic acid (1.44 g) was added methyl-sulfonic acid (30 mL). The mixture was heated slowly up to 100° C. under nitrogen. The reaction mixture was stirred at 100° C. for 1 hour. The solution was poured into ice, and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water solution, water and brine. Evaporation and chromatography (silica gel, hexane-ethyl acetate 10% to 25%) gave 1.77 g of 6-hydroxy-5,7,8-trimethyl-chroman-2-one.

Workup

  1. additionThe solution was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate water solution, water and brine
  4. customEvaporation and chromatography (silica gel, hexane-ethyl acetate 10% to 25%)

Sources & evidence

ORD record
ord-50e884a726b04268a29f0971abcc353d
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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