2,5-Dihydroxybenzoic acid → 8-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

HRID 424312

Reaction equation

HRID 424312 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].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21].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][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)=[O:21])=[O:5]

Participants

5

Reactant 3

HCID 34692,5-Dihydroxybenzoic acidHCID 6342AcetonitrileHCID 590050482-Furylmethyl 8-bromooctanoate

Product 1

HCID 590050178-(2-Furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dihydroxybenzoic acid (4.8 g), 1,8-diazobicyclo[5.5.0]undec-7-ene (4.7 g), 2-furylmethyl 8-bromooctanoate (7.8 g) and acetonitrile (150 ml) was heated, under reflux for 18 h. The cooled reaction mixture was added to water (500 ml) and extracted with ethyl acetate (3×200 ml). The combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuum. The residue (8.4 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (5:1) as eluent, to give 8-(2-furylmethoxy)-8-oxooctyl 2,5-dihydroxybenzoate as colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (150 ml) and water (2×20 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customThe residue (8.4 g) was purified by column flash chromatography on silica gel

Sources & evidence

ORD record
ord-a0d12cd9d8634c1b8714299d4f590676
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Linked notes

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