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

HRID 1834533Notes

Reaction equation

HRID 1834533 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, 8parts 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°-74° 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-0557b1ed9a074d62971a21bc14f99e0d
Source dataset
uspto-grants-1978_01
Patent number
US04070481

Reaction notes

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