Acetone → HCID 15124394, compound

HRID 1460825Notes

Reaction equation

HRID 1460825 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CC(C)=O.[CH2:13]([OH:15])[CH3:14].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[C:26]1([CH3:32])[CH:31]=C[CH:29]=[CH:28][CH:27]=1>>[CH2:13]([O:15][C:28]1([CH3:29])[CH2:27][C:26]([CH3:32])([CH3:31])[C:8]2[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=2)[O:2]1)[CH3:14]

Participants

7

Reactant 6

HCID 180AcetoneHCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 5054ResorcinolHCID 516892Sodium Bicarbonate

Product 1

HCID 15124394HCID 15124394, compoundYield 21.4%

Procedure

50 ml stainless steel autoclave was charged with 2.2 g (20 mmol) of resorcin, 2.32 g (40 mmol) of acetone, 9.2 g (200 mmol) of ethanol, 0.2 g (2 mmol) of conc. sulfuric acid and 10 ml of toluene, then sealed and allowed to react at 100° 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 1.01 g (21.4%) of 2-ethoxy-7-hydroxy-2,4,4-trimethylchroman as a colorless viscous liquid.

Workup

  1. customsealed
  2. customto react at 100° 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-4cf236260d6143f58ce2674f093b8d47
Source dataset
uspto-grants-1991_12
Patent number
US05072007

Reaction notes

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