Acetyl chloride → 3-Acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone

HRID 26236Notes

Reaction equation

HRID 26236 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([OH:25])=[C:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:7]2=[O:12].[O:27]1CC[CH2:29][CH2:28]1.[H-].[Na+].C(Cl)(=O)C>C(Cl)Cl>[C:28]([O:25][C:5]1[C:4](=[O:26])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[Cl:1])[C:7](=[O:12])[C:6]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:27])[CH3:29]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran4×HCID 24758Sodium hydrideHCID 178442826HCID 178442826, compound

Product 1

HCID 213252433-Acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.95 parts of 5-chloro-2-dodecyl-3-hydroxy-1,4-naphthoquinone in 20 parts of anhydrous tetrahydrofuran was added under nitrogen to a mixture of 0.0635 parts of dispersed sodium hydride in 40 parts of tetrahydrofuran with stirring at room temperature. After 45 minutes of stirring, a solution of 0.275 parts of acetyl chloride in 30 parts of tetrahydrofuran was added and the mixture stirred for 5 hours. The tetrahydrofuran was stripped under reduced pressure and the residue taken up in methylene chloride and then washed with water, 10% hydrochloric acid, four more times with water, dried over sodium sulfate and stripped. The resulting yellow solid was purified by column chromatography on silica gel using 1-chlorobutane as eluent. Solvent removal gave 0.9 parts of 3-acetoxy-5-chloro-2-dodecyl-1,4-naphthoquinone, m.p. 57°-59° C.

Workup

  1. stirringAfter 45 minutes of stirring
  2. stirringthe mixture stirred for 5 hours
  3. washwashed with water, 10% hydrochloric acid, four more times with water
  4. dry with materialdried over sodium sulfate
  5. customThe resulting yellow solid was purified by column chromatography on silica gel
  6. customSolvent removal

Sources & evidence

ORD record
ord-a23e3a8557d14704af10c6d5c0d72db7
Source dataset
uspto-grants-1979_04
Patent number
US04148918

Reaction notes

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