Acetic Acid → HCID 13234999, compound

HRID 1284883Notes

Reaction equation

HRID 1284883 reaction equation
[CH2:1]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]=1[OH:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(O)(=[O:29])C>O>[CH2:1]([C:16]1[C:17](=[O:26])[C:18]2[C:23]([C:24](=[O:29])[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 20250607HCID 20250607, compound2×

Product 1

HCID 13234999HCID 13234999, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Pentadecyl-1-naphthol (48 , 135 mmol) was dissolved in acetic acid with slight warming. Chromic oxide (55.5 g, 555 mmol) was dissolved in 50 ml water and then 50 ml acetic acid was added. This chromic oxide solution was then added dropwise with stirring to the solution of the pentadecylnaphthol maintaining the temperature between 45°-50° C. The mixture was then stirred for several hours while slowly cooling to room temperature. The pentadecylnaphthoquinone, which had crystallized from solution was filtered off, washed with acetic acid, water, and air dried. Yield: 24 g (48 percent). (Method of L. F. Fieser et al, J. Am. Chem. Soc., 74, 3910 (1952)).

Workup

  1. customThe pentadecylnaphthoquinone, which had crystallized from solution
  2. filtrationwas filtered off
  3. washwashed with acetic acid, water, and air
  4. customdried

Sources & evidence

ORD record
ord-17ab1ede57b24b6c8caad83c5e6ea5da
Source dataset
uspto-grants-1986_01
Patent number
US04564577

Reaction notes

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