Hydrochloric Acid → 1,3-Dinaphthyl-1,3-propanedione

HRID 1827348

Reaction equation

HRID 1827348 reaction equation
[NH2-].[Na+].[C:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].COC([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=O.Cl.C[CH2:32][O:33]CC>>[C:23]1([C:32](=[O:33])[CH2:4][C:3]([C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)=[O:5])[C:22]2[C:27](=[CH:28][CH:29]=[CH:20][CH:21]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136631-AcetylnaphthaleneHCID 24533Sodium amideHCID 137605Methyl 2-naphthoate

Product 1

HCID 152593661,3-Dinaphthyl-1,3-propanedione

Procedure

4.75 gr of 50% slurry of sodium amide was suspended in 150 ml of anhydrous ether in a 250 ml round bottom flask that was equipped with a magnetic stir bar and a condenser. To this suspension was added 5.1 gr of solid acetonaphthone and continued stirring for 5 min at room temperature. After 5 minutes, 5.58 gr of methyl-2-naphthoate was added in one lot. At this point, the reaction flask was transferred to an oil bath and the bath temperature was raised so that the contents reflux gently in ether for 3 hours. The contents were then poured onto 300 gr of solid ice. On acidification with conc. HCl, solid product fell out of solution. The solid product was filtered and recrystallized in ether/methanol mixture.

Workup

  1. customthat was equipped with a magnetic stir bar and a condenser
  2. waitAfter 5 minutes
  3. customAt this point, the reaction flask was transferred to an oil bath
  4. temperaturethe bath temperature was raised so that the contents
  5. additionThe contents were then poured onto 300 gr of solid ice
  6. filtrationThe solid product was filtered
  7. customrecrystallized in ether/methanol mixture

Sources & evidence

ORD record
ord-9f0f95347bfe4bd7a6d3c92cbae0449e
Source dataset
uspto-grants-2006_05
Patent number
US07053249B2

Linked notes

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