Sulfuric Acid → HCID 14577959, compound

HRID 1904544Notes

Reaction equation

HRID 1904544 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[C:6]1([CH:13]=[CH:12][CH:11]=[C:9]([OH:10])[CH:8]=1)O.[CH:14](OC)(OC)[O:15]C.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>>[OH:4][C:3]1[CH:5]=[CH:6][C:13]2[CH2:12][CH2:11][C:9]([O:15][CH3:14])([CH3:8])[O:10][C:2]=2[CH:1]=1

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 5054ResorcinolHCID 6570Methyl vinyl ketoneHCID 9005Trimethyl orthoformateHCID 516892Sodium Bicarbonate

Product 1

HCID 14577959HCID 14577959, compoundYield 70%

Procedure

Methyl vinyl ketone (7.7 g) was added dropwise under ice cooling to a solution composed of 11 g of resorcinol, 11.7 g of trimethyl orthoformate and 0.1 ml of conc. sulfuric acid. After the addition, the mixture was stirred at room temperature for 2 hours. The reaction mixture was neutralized with a saturated aqueous solution of sodium bicarbonate, and then extracted with ethyl acetate. The residue left after evaporation of the solvent as purified by column chromatography to give 12.5 g (yield 70%) of the desired product as colorless crystals (melting point 107°-108° C.).

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. waitThe residue left
  4. customafter evaporation of the solvent
  5. customas purified by column chromatography

Sources & evidence

ORD record
ord-7ff1bf9e213549dbaba481e3369437d4
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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