Acetone → HCID 15590645, compound

HRID 1460824Notes

Reaction equation

HRID 1460824 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CC(C)=O.CO.S(=O)(=O)(O)O.[C:20]([O-:23])(O)=O.[Na+].[C:25]1([CH3:31])[CH:30]=C[CH:28]=[CH:27][CH:26]=1>>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:25]([CH3:31])([CH3:30])[CH2:26][C:27]([O:23][CH3:20])([CH3:28])[O:5]2)=[CH:7][CH:8]=1

Participants

7

Reactant 6

HCID 180AcetoneHCID 887MethanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 5054ResorcinolHCID 516892Sodium Bicarbonate

Product 1

HCID 15590645HCID 15590645, compoundYield 17%

Procedure

30 ml glass autoclave was charged with 2.2 g (20 mmol) of resorcin, 2.32 g (40 mmol) of acetone, 3.2 g (100 mmol) of methanol, 0.2 g (2 mmol) of conc. sulfuric acid and 10 ml of toluene, then sealed, and allowed to react at 70° C. for 4 hours. Then, the reaction mixture was cooled to room temperature, neutralized with saturated NaHCO3, washed with water, and toluene was distilled off under reduced pressure. The residue was purified by column chromatography on silicagel using hexane-ethyl acetate as an eluent to give 0.75 g (17.0%) of 7-hydroxy-2-methoxy-2,4,4-trimethylchroman as a colorless oil.

Workup

  1. customsealed
  2. customto react at 70° C. for 4 hours
  3. washwashed with water, and toluene
  4. distillationwas distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-dbe5db6ee48b4e36b7099585cf6b3118
Source dataset
uspto-grants-1991_12
Patent number
US05072007

Reaction notes

Loading…