Acetyl chloride → HCID 21829927, compound

HRID 1600697Notes

Reaction equation

HRID 1600697 reaction equation
[C:1]([C:5]1[O:10][C:9](=[O:11])[C:8]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])=[C:7]([OH:21])[C:6]=1[Cl:22])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:30](Cl)(=[O:32])[CH3:31]>C(OCC)(=O)C.C1(C)C=CC=CC=1.CC(C)=O>[C:30]([O:21][C:7]1[C:6]([Cl:22])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:10][C:9](=[O:11])[C:8]=1[C:12]1[C:13]([CH3:20])=[CH:14][C:15]([CH3:19])=[CH:16][C:17]=1[CH3:18])(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54714387HCID 54714387, compound

Product 1

HCID 21829927HCID 21829927, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 20247278Toluene acetoneSolvent

Conditions

Temperature
20 °C

Procedure

6.4 g (20 mmol) of 6-tert-butyl-5-chloro-4-hydroxy-3-(2,4,6-trimethylphenyl)-2-pyrone (Ex. I-a-4) are initially charged in 50 ml of ethyl acetate. At 20° C., 2.02 g (20 mmol) of triethylamine are added, and at 0° C. a solution of 1.6 g (20 mmol) of acetyl chloride in 20 ml of ethyl acetate is added dropwise. The mixture is subsequently stirred at 20° C. for 20 h. Precipitated triethylamine hydrochloride is filtered off with suction and washed with ethyl acetate. The combined mother liquors are washed twice with 50 ml of half-concentrated sodium chloride solution each time, dried over magnesium sulphate and concentrated under reduced pressure. 7.2 g of crude product are obtained. Flash chromatography over silica gel 60 (35-70 μm) using toluene:acetone 30:1 as eluent yields 4.1 g (57% of theory) of 4-acetyloxy-6-tert-butyl-5-chloro-(2,4,6-trimethylphenyl)-2-pyrone of melting point 116-118° C.

Workup

  1. filtrationPrecipitated triethylamine hydrochloride is filtered off with suction
  2. washwashed with ethyl acetate
  3. washThe combined mother liquors are washed twice with 50 ml of half-concentrated sodium chloride solution each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custom7.2 g of crude product are obtained

Sources & evidence

ORD record
ord-fe1446e5c4bb43ed81c566bf22e477ea
Source dataset
uspto-grants-1999_11
Patent number
US05977029

Reaction notes

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