Acetic Anhydride → HCID 23046874, compound

HRID 2107835Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][C:13](=[O:16])[CH2:14][CH3:15])=[CH:7][CH:8]=2)[CH:3]=1.C(OC(=O)C)(=[O:19])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:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH:1]=[O:19])=[CH:3]2)=[CH:8][CH:7]=1)(=[O:16])[CH2:14][CH3:15]

Participants

Conditions

Temperature: 180 °C

Procedure

The same reactor as used in the second half of Example 1 was charged with 11.4 parts of the resulting 2-methyl-7-propionyloxynaphthalene crystals, 90 parts of acetic acid, 10 parts of acetic anhydride, 0.249 part (Co=5990 we. ppm) of cobalt acetate tetrahydrate, 0.245 part (Mn=550 wt. ppm) of manganese acetate tetrahydrate, and 0.250 part (Br=2040 wt. ppm) of ammonium bromide, and pressurized to 8 kg/cm2 -G. The mixture was heated to 180° C., and air was introduced into the reactor at a rate of 10 Nl/hr. The reaction was terminated when the absorption of oxygen ceased. The reaction time was 2 hours. The reactor was cooled, and the contents were withdrawn and analyzed. The conversion of 2-methyl-7-propionyloxynaphthalene was 100 mole %, and the yield of 7-propionyloxy-2-naphthoic acid was 51.0 mole % (selectivity 51 mole %). At this time, 19 mole % of 7-propionyloxy-2-naphthaldehyde was formed.

Workup

customThe reaction was terminated when
customthe absorption of oxygen
temperatureThe reactor was cooled
customthe contents were withdrawn

Sources & evidence

ORD record: ord-d581a6d63815480c8ee05dd68e77e683
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04935537

Reaction notes

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