2-Aminophenol → Benzoic Acid

HRID 1614842Notes

Reaction equation

HRID 1614842 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1.[NH2:13][C:14]1C=CC=C[C:15]=1O.[OH:21][C:22]1[CH:31]=C[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:32]([OH:34])=[O:33])[CH:28]=2)C=1.C(O[C:39](=[O:41])[CH3:40])(=O)C>CN(C)C=O>[C:22]1(=[O:21])[N:13]([C:3]2[CH:2]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])[C:39](=[O:41])[CH:40]=[CH:31]1.[C:32]([OH:34])(=[O:33])[C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1.[C:5]([OH:7])(=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1.[CH:14]#[CH:15].[C:1]1(=[O:12])[NH:13][C:39](=[O:41])[CH:40]=[CH:2]1

Participants

9

Reactant 4

HCID 58012-AminophenolHCID 7918Acetic AnhydrideHCID 8496Isophthalic AcidHCID 855576-Hydroxy-2-naphthoic acid

Product 4

HCID 243Benzoic AcidHCID 10935MaleimideHCID 2485962-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)benzoic acidHCID 68634872Acetylene benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
320 °C

Procedure

Alternatively, the liquid crystalline thermoset oligomer can be prepared by a bulk polymerization process in accordance with the following procedure. In another exemplary method, isophthalic acid, aminophenol, 2-hydroxy-6-naphthoic acid and acetic anhydride are slowly heated to 150° C. with stirring in a reactor. The mixture is brought to reflux for a predetermined time period. Acetic acid as a by-product and unreacted acetic anhydride are removed from the reaction mixture. Next, 4-hydroxybenzoic acid is added, and the temperature is further raised to 320° C. and the reaction temperature is maintained which allows the reaction to proceed, to give a liquid crystal oligomer having one or two terminal alcohol groups at one or both ends of the backbone. The liquid crystal oligomer is dissolved in a proper solvent (e.g., N,N-dimethylformamide, abbreviated “DMF”), and then a compound (e.g., maleimidobenzoic acid, nadimide benzoic acid, or acetylene benzoic acid) capable of providing thermally crosslinkable reactive groups (e.g., maleimide, nadimide or acetylene groups) is added to the solution. The mixture is allowed to react to give the liquid crystalline thermoset oligomer having one or two thermally crosslinkable reactive groups at one or both ends of the backbone thereof.

Workup

  1. customAlternatively, the liquid crystalline thermoset oligomer can be prepared by a bulk polymerization process in accordance with the following procedure
  2. temperatureto reflux for a predetermined time period
  3. customAcetic acid as a by-product and unreacted acetic anhydride are removed from the reaction mixture
  4. additionNext, 4-hydroxybenzoic acid is added
  5. temperaturethe reaction temperature is maintained which
  6. customthe reaction
  7. customto give a liquid crystal oligomer

Sources & evidence

ORD record
ord-a0e4f3e74c53462898db953c8a49c170
Source dataset
uspto-grants-2014_07
Patent number
US08765012B2

Reaction notes

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