2,5-Dihydroxybenzoic acid → 2,3-Dihydroxybenzoic Acid

HRID 1168902Notes

Reaction equation

HRID 1168902 reaction equation
O[C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[O:27]1CCCC1>>[CH:10]1[CH:9]=[C:8]([OH:11])[C:7]([OH:27])=[C:3]([C:4]([OH:6])=[O:5])[CH:2]=1

Participants

4

Reactant 3

HCID 34692,5-Dihydroxybenzoic acid2×HCID 8028Tetrahydrofuran2×HCID 10868Dicyclohexylcarbodiimide2×

Product 1

HCID 192,3-Dihydroxybenzoic Acid

Procedure

2,5-dihydroxy benzoic acid (DHBA) is first activated by treatment with dicyclohexylcarbodiimide (DCC) and NHS in tetrahydrofurane (THF). To a stirred solution of 9.25 g (60 mmole) DHBA in 450 ml of THF was added 7.14 g (62 mmole) NHS and 12.8 g (62 mmole) DCC. After filtering off the formed dicyclohexylurea, the solution was concentrated by vacuum evaporation until crystallisation of the DHBA-MHS ester started. The solution was stored at 5° C. for 12 hrs and the resulting DHBA-NHS precipitate was collected by filtration. After drying the yield of the synthesis was 70%.

Workup

  1. filtrationAfter filtering off the formed dicyclohexylurea
  2. concentrationthe solution was concentrated by vacuum evaporation until crystallisation of the DHBA-MHS ester
  3. filtrationthe resulting DHBA-NHS precipitate was collected by filtration
  4. customAfter drying the yield of the synthesis

Sources & evidence

ORD record
ord-bfb784758acf492484f14f51ac6b5a0b
Source dataset
uspto-grants-2003_09
Patent number
US06627667B2

Reaction notes

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