2,5-Dihydroxybenzoic acid → HCID 59005037, compound

HRID 424314Notes

Reaction equation

HRID 424314 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][CH3:19].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][CH3:19])=[O:5]

Participants

5

Reactant 3

HCID 34692,5-Dihydroxybenzoic acidHCID 6342AcetonitrileHCID 123691-Bromoheptane

Product 1

HCID 59005037HCID 59005037, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dihydroxybenzoic acid (28 g), 1,8-diazobicyclo[5.5.0]undec-7-ene (27.6 g), 1-bromo-heptane (39 g) and acetonitrile (380 ml) was heated, under reflux for 18 h. The cooled reaction mixture was added to water (1000 ml) and extracted with ethyl acetate (3×400 ml). The combined organic layers were washed with 1N-hydrochloric acid (300 ml) and water (2×400 ml), dried over magnesium sulphate and filtered. The solvent was removed in vacuum. The residue (40 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (9:1) as eluent, to give heptyl 2,5-dihydroxybenzoate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×400 ml)
  5. washThe combined organic layers were washed with 1N-hydrochloric acid (300 ml) and water (2×400 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed in vacuum
  9. customThe residue (40 g) was purified by column flash chromatography on silica gel

Sources & evidence

ORD record
ord-d19e368ab99342eea5528ede84fb239a
Source dataset
uspto-grants-2012_01
Patent number
US08105662B2

Reaction notes

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