Acetyl chloride → 6-(2,4-Dichlorophenyl)-2-oxo-5-hexene-4-yl Acetate

HRID 1285595Notes

Reaction equation

HRID 1285595 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH:13]=[CH:14][CH:15]([OH:20])[CH2:16][C:17](=[O:19])[CH3:18]>N1C=CC=CC=1>[C:1]([O:20][CH:15]([CH:14]=[CH:13][C:7]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=1[Cl:5])[CH2:16][C:17](=[O:19])[CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 543593126-(2,4-Dichlorophenyl)-4-hydroxy-5-hexene-2-one

Product 1

HCID 544676676-(2,4-Dichlorophenyl)-2-oxo-5-hexene-4-yl AcetateYield 87.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

Acetyl chloride (1.2 ml, 16.5 mmole) was added dropwise to a stirred solution of 6-(2,4-dichlorophenyl)-4-hydroxy-5-hexene-2-one (3.9 g, 15 mmole) in pyridine (60 ml) at 0° C. The ice bath was removed, and the reaction mixture was stirred at 20° C. for 2 hours and then diluted with ether (300 ml). The ether solution was washed with 1N HCl (3×300 ml) and saturated NaHCO3, dried over MgSO4, filtered and evaporated. The residual pale amber oil (4.1 g) was chromatographed on a 50 mm column with 15 cm of silica gel (230-400 mesh). Elution with methylene chloride (2 L) provided the title compound as a pale yellow oil (3.95 g, 87%): pmr (CDCl3) δ2.03 (3H, s), 2.17 (3H, s), 2.83 (2H, dd).

Workup

  1. customThe ice bath was removed
  2. additiondiluted with ether (300 ml)
  3. washThe ether solution was washed with 1N HCl (3×300 ml) and saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual pale amber oil (4.1 g) was chromatographed on a 50 mm column with 15 cm of silica gel (230-400 mesh)
  8. washElution with methylene chloride (2 L)

Sources & evidence

ORD record
ord-30e94ffb9c984e4bbaa4693d8772dc5f
Source dataset
uspto-grants-1986_01
Patent number
US04567289

Reaction notes

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