Ethanol → Diethyl 1,4-diethoxynaphthalene-2,3-dicarboxylate

HRID 461445Notes

Reaction equation

HRID 461445 reaction equation
I[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].[Na].[CH2:27](O)[CH3:28]>[O-]CC.[Na+]>[CH2:27]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:2][CH3:3])=[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])[CH3:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylateHCID 5360545Sodium

Product 1

HCID 21393755Diethyl 1,4-diethoxynaphthalene-2,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

Iodoethane (70 g) was added to a solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (35 g) in ethanolic sodium ethoxide, prepared from sodium (7.6 g) and ethanol (250 ml), and the mixture was heated under reflux for 3 hours. After keeping overnight at room temperature, the mixture was poured onto ice-hydrochloric acid (500 ml). The oil was separated, washed with aqueous sodium bicarbonate and crystallised from ethanol to give diethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate, (IV) m.p. 68°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additionthe mixture was poured onto ice-hydrochloric acid (500 ml)
  4. customThe oil was separated
  5. washwashed with aqueous sodium bicarbonate
  6. customcrystallised from ethanol

Sources & evidence

ORD record
ord-e280d71c7d034381aa4fecbb5b3e170a
Source dataset
uspto-grants-1977_12
Patent number
US04062955

Reaction notes

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