4-Hydroxybenzoic Acid → 2,4-Dihydroxybenzoic Acid

HRID 927850Notes

Reaction equation

HRID 927850 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]1[CH2:15][O:14][CH2:13][CH2:12]1.[CH3:16][OH:17]>>[OH:14][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:2]=1)[C:6]([OH:8])=[O:7].[OH:17][C:16]1[CH:10]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=1[C:6]([OH:8])=[O:7].[OH:17][C:13]1[CH:12]=[CH:11][C:15]([OH:14])=[CH:4][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 887Methanol2×HCID 8028Tetrahydrofuran

Product 3

HCID 14912,4-Dihydroxybenzoic AcidHCID 34692,5-Dihydroxybenzoic acidHCID 74203-Hydroxybenzoic Acid

Procedure

Crystallization processes performed with hydroxybenzoic acids gave different results, for example for crystallization of saturated solutions of 4-hydroxybenzoic acid in methanol resulted in a new phase, as shown in FIG. 1. Similarly using methanol or THF, NSF were obtained with the co-formers 3-hydroxybenzoic acid (FIG. 10), 2,4-dihydroxybenzoic acid (FIG. 11), 2,5-dihydroxybenzoic acid (FIGS. 6A, 6B and 6C), 3,4-hydroxybenzoic acid (FIGS. 12A and 12B) and 3,5-hydroxybenzoic acid (FIG. 13).

Workup

  1. customCrystallization
  2. customgave different results
  3. customresulted in a new phase

Sources & evidence

ORD record
ord-9dbe10e06db448b8a50a0b69ef73bb04
Source dataset
uspto-grants-2016_03
Patent number
US09290492B2

Reaction notes

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