Dichloromethane → Acequinocyl

HRID 973250Notes

Reaction equation

HRID 973250 reaction equation
[CH2:1]([C:13]1[C:14](=[O:25])[C:15]2[C:20]([C:21](=[O:24])[C:22]=1[OH:23])=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].C(Cl)Cl>O>[C:33]([O:23][C:22]1[C:21](=[O:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:25])[C:13]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178442823HCID 178442823, compound

Product 1

HCID 93315Acequinocyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 parts of 2-n-dodecyl-3-hydroxy-1,4-naphthoquinone, 0.81 parts of triethylamine, 0.63 parts of acetyl chloride and 50 parts of methylene chloride was stirred at room temperature for 30 hours. The resulting mixture was distributed between methylene chloride and water. The methylene chloride layer was separated, dried over magnesium sulfate, then filtered and evaporated under reduced pressure. The residue was crystallized from petroleum ether (b.p. 30°-60°) to give 1.2 parts of 3-acetoxy-2-n-dodecyl-1,4-naphthoquinone, m.p. 57°-58° C.

Workup

  1. customThe methylene chloride layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was crystallized from petroleum ether (b.p. 30°-60°)

Sources & evidence

ORD record
ord-6d8e186d5c774fcda3f2bf0214a89432
Source dataset
uspto-grants-1977_10
Patent number
US04055661

Reaction notes

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