Sulfuric Acid → 4-cyclopropanecarbonylphenol

HRID 1469867Notes

Reaction equation

HRID 1469867 reaction equation
ClCC[CH2:4][C:5]1(O)[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH2:6]1.[OH-:14].[Na+].S(=O)(=O)(O)O.C([O:24][CH2:25][CH3:26])(=O)C>>[CH:9]1([C:10]([C:5]2[CH:4]=[CH:26][C:25]([OH:24])=[CH:7][CH:6]=2)=[O:14])[CH2:8][CH2:11]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 89752875HCID 89752875, compound

Product 1

HCID 10515124-cyclopropanecarbonylphenolYield 86%

Procedure

4-Chloropropyl(4-hydroxyphenyl)methanone (25.1 g, 127 mmol) was added to a 2 N aqueous solution of sodium hydroxide (283 mL, 566 mmol) in several portions under ice cooling. The reaction mixture was allowed to warm up to room temperature, and was stirred for 6 hours, and then dilute sulfuric acid (1.8 N) was added to the reaction mixture under ice cooling until a pH value of 2 was obtained. The reaction mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with water and brine, and then was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→2:1, v/v) to give the title compound (17.7 g, yield: 86%).

Workup

  1. customwas obtained
  2. extractionThe reaction mixture was subjected to extraction twice with ethyl acetate
  3. customThe organic layer thus obtained
  4. washwas washed with water and brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-4ec8ff578e6e404bb9b9bb8a1b4e35f1
Source dataset
uspto-grants-2015_04
Patent number
US09006273B2

Reaction notes

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