Hydrochloric Acid → 1,1'-(Naphthalene-2,6-diyl)bis(4,4-dimethylpentane-1,3-dione)

HRID 1613009Notes

Reaction equation

HRID 1613009 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13]C)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17]C)=O.[CH3:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].[H-].[Na+].Cl>O1CCCC1>[CH3:22][C:21]([CH3:24])([CH3:23])[C:20](=[O:25])[CH2:19][C:11]([C:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:15](=[O:17])[CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:1]=2)[CH:6]=1)=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 24758Sodium hydrideHCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Product 1

HCID 197775741,1'-(Naphthalene-2,6-diyl)bis(4,4-dimethylpentane-1,3-dione)Yield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.0 gm of dimethyl 2,6-naphthalene dicarboxylate and 2.8 gm of pinacolone, which had been dissolved in 25 ml of anhydrous tetrahydrofuran, 1.1 gm of 60% sodium hydride was added. The mixture was reacted at 60° C. for 4 hours while stirring. The reaction mixture was poured into ice-cooled 2N hydrochloric acid. Organic substances were extracted using chloroform and, after evaporating the solvent, recrystallized in a mixed solvent of chloroform-methanol to obtain 2.1 gm of the target compound as pale yellow

Workup

  1. customThe mixture was reacted at 60° C. for 4 hours
  2. additionThe reaction mixture was poured into ice-
  3. extractionOrganic substances were extracted
  4. customafter evaporating the solvent
  5. customrecrystallized in a mixed solvent of chloroform-methanol

Sources & evidence

ORD record
ord-02f8d1c66b424239a1e0a465280eac4b
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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