Sulfuric Acid → HCID 19104226, compound

HRID 1973451Notes

Reaction equation

HRID 1973451 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:17]=[CH:18][CH:19]=1)[CH2:9][CH:10](C([O-])=O)C([O-])=O)(=O)C.[OH-:20].[Na+].S(=O)(=O)(O)O.[O:27]1[CH2:32]COCC1>>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:9]([CH3:10])[C:32]([OH:27])=[O:20])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20386024HCID 20386024, compound

Product 1

HCID 19104226HCID 19104226, compound

Procedure

Refer to Chart G. A solution of m-(acetoxymethyl)-benzylmalonate, dimethyl ester (Preparation 3, 9.16 g.) in 45 ml. of dioxane is treated with 137 ml. of 10% sodium hydroxide at about 25° C. for 15 min. The mixture is acidified to pH 1.0 with sulfuric acid, treated with an additional 3 ml. of sulfuric acid, and heated at reflux for about 36 hr. The mixture is cooled, diluted with 430 ml. brine and extracted with chloroform. The extract is washed with brine, dried over magnesium sulfate, and concentrated. Yield of title compound: 4.31 g., having NMR peaks at 2.40-3.18, 4.58, 7.17, and 7.53δ.

Workup

  1. additiontreated with an additional 3 ml
  2. temperatureat reflux for about 36 hr
  3. temperatureThe mixture is cooled
  4. additiondiluted with 430 ml
  5. extractionbrine and extracted with chloroform
  6. washThe extract is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ec041ccd25ad46659fbaf0a8596b8af5
Source dataset
uspto-grants-1976_12
Patent number
US03997566

Reaction notes

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