2,5-Dihydroxybenzoic acid → HCID 22555023, compound

HRID 2224037Notes

Reaction equation

HRID 2224037 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].C(N(CC)CC)C.[C:15]([OH:25])(=[O:24])[C:16]1[C:17](=[CH:19][CH:20]=[C:21]([CH:23]=1)[OH:22])[OH:18].C(OCC)(=O)C>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([O:22][C:21]1[CH:20]=[CH:19][C:17]([OH:18])=[C:16]([CH:23]=1)[C:15]([OH:25])=[O:24])=[O:6]

Participants

6

Reactant 4

HCID 34692,5-Dihydroxybenzoic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 702254-Bromobutyryl chloride

Product 1

HCID 22555023HCID 22555023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 4-bromobutyrylchloride (3 g, 16.17 mmoles) in tetrahydrofuran (50 ml), cooled at 0° C., triethylamine (4.5 ml, 32.34 mmoles) and then gentisic acid (2.4 g, 16.16 mmol) are dropped under stirring. It is allowed to react at 0° C. for 4 hours, under stirring, then it is evaporated at reduced pressure. The obtained crude product is treated with ethyl acetate, the organic phase is washed with HCl 1% and then brine. The organic phase is anhydrified with sodium sulphate and dried. The obtained residue is purified by chromatography on silica gel column, eluting with methylene chloride/methanol 95/5, obtaining the 5-(4-bromobutyryloxy)-2-hydroxy-benzoic acid.

Workup

  1. customto react at 0° C. for 4 hours
  2. stirringunder stirring
  3. customit is evaporated at reduced pressure
  4. customThe obtained crude product
  5. washthe organic phase is washed with HCl 1%
  6. customdried
  7. customThe obtained residue is purified by chromatography on silica gel column
  8. washeluting with methylene chloride/methanol 95/5

Sources & evidence

ORD record
ord-cc05530cf68847d28047fe5636620c1f
Source dataset
uspto-grants-2008_05
Patent number
US07378412B2

Reaction notes

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