6-(Acetyloxy)-2-naphthalenecarboxylic acid → HCID 14848179, compound

HRID 2107833Notes

Reaction equation

HRID 2107833 reaction equation
CC1C=CC2C(=CC=C(OC(=O)C)C=2)C=1.[C:16]([O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([C:30](O)=[O:31])[CH:24]=[CH:23]2)(=[O:18])[CH3:17]>>[C:16]([O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([CH:30]=[O:31])[CH:24]=[CH:23]2)(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 870386-(Acetyloxy)-2-naphthalenecarboxylic acidHCID 13609265HCID 13609265, compound2×

Product 1

HCID 14848179HCID 14848179, compound

Procedure

The 2-methyl-6-acetyloxynaphthalene obtained in the first half of Example 1 was not recrystallized from acetic anhydride prior to oxidation, but was directly oxidized with molecular oxygen in the presence of the same catalyst as in Example 1 in the same reactor as in Example 1. The reaction time was 2.4 hours. After the reaction, the product was analyzed. The conversion of 2-methyl-6-acetyloxynaphthalene was 55.5 mole %, and the yield of 6-acetyloxy-2-naphthoic acid was 40.0 mole % (selectivity 72 mole %). At this time, 8.88 mole % of 6-acetyloxy-2-naphthaldehyde was formed.

Workup

  1. customwas not recrystallized from acetic anhydride
  2. customAfter the reaction

Sources & evidence

ORD record
ord-d1c15946363841bf9c159ef00ba42a6f
Source dataset
uspto-grants-1990_06
Patent number
US04935537

Reaction notes

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