Ethyl Bromide → Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

HRID 222429Notes

Reaction equation

HRID 222429 reaction equation
Br[CH2:2][CH3:3].[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:3]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

Product 1

HCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylateYield 60.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Bromoethane (0.359 g, 3.29 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (1 g, 3.29 mmol) and potassium carbonate (0.454 g, 3.29 mmol) in acetone (25 ml). The reaction mixture was refluxed for 24 hours under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and water. The combined organics were washed with water and dried over magnesium sulphate. The orange oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-10%) in hexane to give the title compound as a clear oil (0.661 g, 1.99 mmol). LC/MS: Rt=3.63, [MH]− 331.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and water
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe orange oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-10%) in hexane

Sources & evidence

ORD record
ord-148d4c5c1a5a4172a12879080866651a
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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