Triethylamine → HCID 21529487, compound

HRID 1657663Notes

Reaction equation

HRID 1657663 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.C(N(CC)CC)C.[CH3:16][O:17][C:18]1[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([Cl:28])[C:19]=1[C:20](Cl)=[O:21]>C1C=CC=CC=1>[CH3:16][O:17][C:18]1[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([Cl:28])[C:19]=1[C:20]([O:7][C:3]1[CH2:4][CH2:5][CH2:6][C:1](=[O:8])[CH:2]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 82609Benzoyl chloride, 3,6-dichloro-2-methoxy-

Product 1

HCID 21529487HCID 21529487, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1,3-Cyclohexanedione (11.2 grams; 0.10 mole), benzene (100 ml) and triethylamine (11.1 grams; 0.10 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer. 2-Methoxy-3,6-dichlorobenzoyl chloride (23.85 grams; 0.10 mole) dissolved in benzene (20 ml) was then added dropwise with stirring. After the addition was completed the reaction mixture was first stirred at ambient temperature for a period of about one hour and then at about 75°C for a period of about 20 minutes. After this time the mixture was cooled to room temperature and was filtered. The filtrate was stripped of benzene under reduced pressure to yield an oil as the residue. This oil was distilled under reduced pressure to yield the desired product 3-oxocyclohex-1-enyl 2-methoxy-3,6-dichlorobenzoate having a boiling point of 199° to 200°C at 0.45 mm of Hg pressure.

Workup

  1. customequipped with a mechanical stirrer
  2. additionwas then added dropwise
  3. additionAfter the addition
  4. stirringwas first stirred at ambient temperature for a period of about one hour
  5. filtrationwas filtered
  6. customto yield an oil as the residue
  7. distillationThis oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-0ddf425938c8470bab6b293e34de0119
Source dataset
uspto-grants-1976_06
Patent number
US03961939

Reaction notes

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