2,5-Dihydroxybenzoic acid → 8-[(2,5-Dihydroxybenzoyl)oxy]octyltetrahydro-2-furancarboxylate

HRID 424311Notes

Reaction equation

HRID 424311 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].[O:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Cl)=[O:18].[I-].[K+].C(#N)C>O>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:17]([CH:13]1[CH2:14][CH2:15][CH2:16][O:12]1)=[O:18])=[O:5]

Participants

6

Reactant 4

HCID 34692,5-Dihydroxybenzoic acidHCID 4875Potassium IodideHCID 6342AcetonitrileHCID 590050228-Chlorooctyl tetrahydro-2-furancarboxylate

Product 1

HCID 590050308-[(2,5-Dihydroxybenzoyl)oxy]octyltetrahydro-2-furancarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dihydroxybenzoic acid (3.9 g), 1,8-diazobicyclo[5.5.0]undec-7-ene (3.8 g), 8-chlorooctyl tetrahydro-2-furancarboxylate (6.0 g), potassium iodide (30.2 g) and acetonitrile (110 ml) was heated, under reflux for 72 h. The cooled reaction mixture was added to water (500 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×15 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuum. The residue (8.0 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (3:1) as eluent, to give 8-[(2,5-dihydroxybenzoyl)oxy]octyltetrahydro-2-furancarboxylate as colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×15 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customThe residue (8.0 g) was purified by column flash chromatography on silica gel

Sources & evidence

ORD record
ord-d0977388ff1b456ba74f695e92e19b4a
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Reaction notes

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