Hydrochloric Acid → HCID 13935419, compound

HRID 235598Notes

Reaction equation

HRID 235598 reaction equation
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[CH3:13][C:14]1[C:23]([CH3:24])=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[CH:25]=[CH:26][C:27](=[O:29])[CH3:28].[OH-].[K+].Cl>C(O)C>[OH:29][C:27]1[CH2:26][CH:25]([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:22]=[C:23]([CH3:24])[C:14]=2[CH3:13])[CH2:2][C:3](=[O:4])[CH:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 53990087HCID 53990087, compound

Product 1

HCID 13935419HCID 13935419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (9.82 g) was added to a solution of sodium metal (1.41 g) in anhdrous absolute ethanol (50 ml). 1-(2,3-Dimethylnaphth-1-yl)but-1-en-3-one (12.5 g) was added to the solution and the mixture was heated under reflux for 2 hr. A slight excess of an aqueous solution of potassium hydroxide was added and the mixture was heated under reflux for a further 5 hr. The hot mixture was acidified by dropwise addition of a dilute aqueous hydrochloric acid solution. After cooling, the product was filtered off and washed with a little diethyl ether to give 3-hydroxy-5-(2,3-dimethylnaphth-1-yl)-cyclohex-2-en-1-one as a white solid, mp 242° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 5 hr
  5. temperatureAfter cooling
  6. filtrationthe product was filtered off
  7. washwashed with a little diethyl ether

Sources & evidence

ORD record
ord-2403800ab39e465093af7e044b329d34
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

Loading…