Hydrochloric Acid → 1-(Naphthalen-1-yl)-3-phenylpropane-1,3-dione

HRID 1827347Notes

Reaction equation

HRID 1827347 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].C[O:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CCOCC>[C:19]1([C:18](=[O:17])[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])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7150Methyl BenzoateHCID 136631-AcetylnaphthaleneHCID 24533Sodium amide

Product 1

HCID 154303601-(Naphthalen-1-yl)-3-phenylpropane-1,3-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

9.5 gr of 50% slurry of sodium amide was suspended in 100 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 10.2 gr of solid acetonaphthone and continued stirring for 5 min at room temperature. After 5 minutes, 8.16 gr of methylbenzoate was added in one lot as a neat liquid. 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 and the pH was adjusted to 7.0 with conc. HCl while stirring. The ether layer was separated and the aqueous layer was extracted with 150 ml aliquots of ether twice. Combined ether layers were dried over a bed of anhydrous sodium sulfate and concentrated on rotavapor to about 100 ml and let it sit at RT. The recrystallized solid was filtered, washed with ether and dried to obtain 10.6 gr of solid diketone.

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. stirringwhile stirring
  7. customThe ether layer was separated
  8. extractionthe aqueous layer was extracted with 150 ml aliquots of ether twice
  9. dry with materialCombined ether layers were dried over a bed of anhydrous sodium sulfate
  10. concentrationconcentrated on rotavapor to about 100 ml
  11. customsit at RT
  12. filtrationThe recrystallized solid was filtered
  13. washwashed with ether
  14. customdried

Sources & evidence

ORD record
ord-025fc7d6980344319bc1a6cd6c6337dd
Source dataset
uspto-grants-2006_05
Patent number
US07053249B2

Reaction notes

Loading…