Hydrochloric Acid → 2-(6-m-Methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione

HRID 1077135Notes

Reaction equation

HRID 1077135 reaction equation
C(N(CC)[CH2:4][CH2:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)C.[CH3:21][CH:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].[Na].Cl>CO.[Cl-].[Na+].O.CCOCC>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][C:6](=[O:18])[CH2:5][CH2:4][C:22]2([CH3:21])[C:26](=[O:27])[CH2:25][CH2:24][C:23]2=[O:28])[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 130052-Methyl-1,3-cyclopentanedioneHCID 5360545SodiumHCID 214855041-(Diethylamino)-6-(3-methoxyphenyl)hexan-3-one

Product 1

HCID 203500022-(6-m-Methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Add the crude methiodide of 1-diethylamino-6-m- methoxyphenylhexan-3-one (2.5 g) in methanol (10 cc) ice-cold to a solution obtained by adding 2-methylcyclopentane-1,3-dione (0.5 g) to an ice-cold solution of sodium (0.21 g) in methaol (10 cc). Allow the reaction mixture to warm to room temperature and leave for 16 hours, after which add N hydrochloric acid (10 cc) and saturated brine (100 cc), and ether-extract the solution. Evaporate the washed and dried extracts to obtain the crude adduct 2-(6-m-methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione as a gum.

Workup

  1. customobtained
  2. customleave for 16 hours
  3. extractionextract the solution
  4. customEvaporate the
  5. washwashed
  6. customdried extracts

Sources & evidence

ORD record
ord-e513a7a5ed3f408dbcb7f7cd2f449b49
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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