Sulfuric Acid → HCID 13253807, compound

HRID 436017Notes

Reaction equation

HRID 436017 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([O:16][CH2:15]2)[C:12]([O-])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:17]([O:20][CH:21](C)C)(C)[CH3:18].S(=O)(=O)(O)[OH:25]>O>[OH:16][CH:15]([C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:9]=1)=[CH2:12])[C:21]([O:20][CH2:17][CH3:18])=[O:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7914Diisopropyl EtherHCID 86734475HCID 86734475, compound

Product 1

HCID 13253807HCID 13253807, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.4 Grams of the ethyl 3-methyl-3-(4-t-butylphenyl-glycidate was dissolved in 60 ml. of dry isopropyl ether. Into this solution, 0.3 g. of sulfuric acid was dropped with ice-cooling, and the resulting mixture was reacted at room temperature for 1 hour. Thereafter, the reaction liquid was poured into water, and then extracted with ether. The ether layer was washed with water and with a saturated aqueous sodium chloride solution in this order, and then dried over anhydrous magnesium sulfate. Subsequently, the ether was evaporated under reduced pressure, and the residue was subjected to distillation to obtain 9.7 g. of the end compound, b.p. 115°- 119° C./0.2 mmHg, yield 78.2% (theoretical value).

Workup

  1. temperaturecooling
  2. customthe resulting mixture was reacted at room temperature for 1 hour
  3. customThereafter, the reaction liquid
  4. extractionextracted with ether
  5. washThe ether layer was washed with water and with a saturated aqueous sodium chloride solution in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customSubsequently, the ether was evaporated under reduced pressure
  8. distillationthe residue was subjected to distillation
  9. customto obtain 9.7 g

Sources & evidence

ORD record
ord-201e5734d1bc479483e8317f8eb9dd05
Source dataset
uspto-grants-1977_02
Patent number
US04007217

Reaction notes

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