2,5-Dihydroxybenzoic acid → HCID 23448409, compound

HRID 1838783Notes

Reaction equation

HRID 1838783 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N12CCCN=C1CCCCC2.[I-].[K+].Cl[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1>O.C(#N)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([C:39]#[N:40])=[CH:37][CH:36]=1)=[O:5]

Participants

7

Reactant 4

HCID 34692,5-Dihydroxybenzoic acidHCID 4875Potassium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23448408HCID 23448408, compound

Product 1

HCID 23448409HCID 23448409, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,5-dihydroxybenzoic acid (4.2 g; 27.5 mmol), 1.8-diazabicyclo[5.4.0]undec-7-ene (4.2 g; 27.5 mmol), potassium iodide (41.0 g; 247 mmol), p-[(8-chlorooctyl)oxy]benzonitrile (6.6 g; 25 mmol) and acetonitrile (100 ml) was heated under reflux for 72 h. The reaction mixture was cooled, poured into water (500 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×150 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuo. The residue was purified by column flash chromatography on silica gel using a toluene/ethyl acetate 80:20 as eluent to give 8.0 g (84%) of 8-(p-cyanophenoxy)octyl 2,5-dihydroxybenzoate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×150 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by column flash chromatography on silica gel using a toluene/ethyl acetate 80:20 as eluent

Sources & evidence

ORD record
ord-5ac1840580d44bc2923b2ead94321af3
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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