Acetic Anhydride → 3-Acetoxy-2-dodecyl-5-methyl-1,4-naphthoquinone

HRID 26231Notes

Reaction equation

HRID 26231 reaction equation
[CH2:1]([C:13]1[C:14](=[O:26])[C:15]2[C:20]([C:21](=[O:24])[C:22]=1[OH:23])=[C:19]([CH3:25])[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:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:23][C:22]1[C:21](=[O:24])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:25])[C:14](=[O:26])[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:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178442825HCID 178442825, compound

Product 1

HCID 213252413-Acetoxy-2-dodecyl-5-methyl-1,4-naphthoquinone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.8 Parts of 2-dodecyl-3-hydroxy-5-methyl-1,4-naphthoquinone, 8 parts of acetic anhydride and 32 parts of pyridine were stirred at room temperature for 16 hours. The resulting mixture was evaporated under reduced pressure to remove the pyridine. The residue was recrystallized from methanol to give 2.5 parts of 3-acetoxy-2-dodecyl-5-methyl-1,4-naphthoquinone, m.p. 69°-75° C.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. customto remove the pyridine
  3. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-916093babf7b48e186344f371eea36fb
Source dataset
uspto-grants-1979_04
Patent number
US04148918

Reaction notes

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