Methanol → HCID 15590645, compound

HRID 1460826Notes

Reaction equation

HRID 1460826 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:9][O:10][C:11](OC)([CH3:13])[CH3:12].CO.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[C:28]1(C)[CH:33]=CC=C[CH:29]=1>>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:28]([CH3:33])([CH3:29])[CH2:12][C:11]([O:10][CH3:9])([CH3:13])[O:5]2)=[CH:7][CH:8]=1

Participants

7

Reactant 6

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 5054ResorcinolHCID 64952,2-DimethoxypropaneHCID 516892Sodium Bicarbonate

Product 1

HCID 15590645HCID 15590645, compoundYield 28.3%

Procedure

30 ml glass autoclave was charged with 2.2 g (20 mmol) of resorcin, 6.2 g (60 mmol) of acetone dimethyl acetal, 6.4 g (200 mmol) of methanol, 0.2 g (2 mmol) of conc. sulfuric acid and 10 ml of toluene, and 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 thus obtained was purified by column chromatography on silicagel using hexane-ethyl acetate as an eluent to give 1.26 g (28.3%) of 7-hydroxy-2-methoxy-2,4,4-trimethylchroman as a colorless oil.

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 thus obtained
  6. customwas purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-fd3a15ddcbc44e4cb8ba2f701ff4cb40
Source dataset
uspto-grants-1991_12
Patent number
US05072007

Reaction notes

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