Water → HCID 67708224, compound

HRID 1608881Notes

Reaction equation

HRID 1608881 reaction equation
[Cl:1][C:2]1([Cl:18])[C@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@@H:3]1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26].O>CCOCC>[Cl:1][C:2]1([Cl:18])[C@H:4]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:3]1[C:11]1[CH:12]=[CH:13][C:14]([O:17][C:25](=[O:27])[CH3:26])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 14469010HCID 14469010, compound2×

Product 1

HCID 67708224HCID 67708224, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 10 mL solution of 1,1-dichloro-cis-2-(p-hydroxyphenyl)-3-phenylcyclopropane (Compound 9) (0.009 mol) and pyridine (0.79 g, 0.01 mol) in Et2O was heated under nitrogen to a gentle reflux, while acetyl chloride (0.78 g, 0.01 mol) was added dropwise slowly via a cannula. A white precipitate was noted immediately, and the mixture was refluxed for 1 h. The reaction flask was cooled while 5 mL of water was added dropwise. Et2O was used to extract the aqueous layer, and the combined Et2O layers were washed with 5% H2SO4, followed b a saturated NaHCO3 solution. Drying with anhydrous Na2SO4, and evaporation of ether gave a dark-yellow oil, which was chromatographed on a silica gel column and eluted with (3:1) CH2Cl2 /petroleum ether to provide a light-yellow oil (0.9 g, 31%). 1H NMR (CDCl3) δ 2.28 (s, 3H, OCOCH3), 3.30 (s, 2H, ArCH), 7.04 (s, 5H, ArH), 7.28 (m, 4H, ArH).

Workup

  1. additionwas added dropwise slowly via a cannula
  2. temperaturethe mixture was refluxed for 1 h
  3. additionwas added dropwise
  4. extractionto extract the aqueous layer
  5. washthe combined Et2O layers were washed with 5% H2SO4
  6. dry with materialDrying with anhydrous Na2SO4, and evaporation of ether
  7. customgave a dark-yellow oil, which
  8. customwas chromatographed on a silica gel column
  9. washeluted with (3:1) CH2Cl2 /petroleum ether

Sources & evidence

ORD record
ord-c8cc7c9394604e7e8c5552de2a993088
Source dataset
uspto-grants-1995_03
Patent number
US05397802

Reaction notes

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