Acetic Anhydride → HCID 14848179, compound

HRID 2292310Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C:13](=[O:15])[CH3:14])[CH:8]=2)[CH:3]=1.C(OC(=O)C)(=[O:18])C.[Br-].[NH4+]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C(O)(=O)C>[C:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:1]=[O:18])[CH:11]=[CH:10]2)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

A 200 cc titanium pressure vessel equipped with a stirrer was charged with 10 parts of 2-methyl-6-acetyloxynaphthalene, 80 parts of acetic acid, 20 parts of acetic anhydride, 0.249 parts (Co=590 wt. ppm) of cobalt acetate tetrahydrate, 0.245 parts (Mn=550 wt. ppm) of manganese acetate tetrahydrate, and 0.250 parts (Br=2040 wt. ppm) of ammonium bromide. The vessel was pressurized with air to 25 kg/cm2 -G, and the mixture was heated to 120° C. Air was introduced into the vessel at a rate of 10 Nl/hr. When the absorption of oxygen ceased, the reaction was terminated. The reaction time was 2.5 hours. The vessel was cooled, and the contents were withdrawn and analyzed. The conversion of 2-methyl-6-acetyloxynaphthalene was 100 mole%, and the yield of 6-acetyloxy-2-naphthoic acid was 68.5 mole% (selectivity 68.5 mole%). At this time, 23.5 mole% of 6-acetyloxy-2-naphthaldehyde was also formed.

Workup

customA 200 cc titanium pressure vessel equipped with a stirrer
customWhen the absorption of oxygen
customthe reaction was terminated
temperatureThe vessel was cooled
customthe contents were withdrawn

Sources & evidence

ORD record: ord-36554beff02c4996b5a06f2fe7c5a105
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801737

Reaction notes

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