Methanol → HCID 21485772, compound

HRID 1077141

Reaction equation

HRID 1077141 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][C:14](=[O:22])[CH2:15][CH2:16]N(CC)CC)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].C(OC1C=C(CCCC(=O)C=C)C=CC=1)(=O)C.[CH3:40][CH:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47].CO>[OH-].[K+].C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][C:14](=[O:22])[CH2:15][CH2:16][C:41]2([CH3:40])[C:45](=[O:46])[CH2:44][CH2:43][C:42]2=[O:47])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 130052-Methyl-1,3-cyclopentanedioneHCID 214854206-m-Acetoxyphenyl-1-diethylaminohexan-3-oneHCID 214855806-m-Acetoxyphenylhex-1-en-3-one

Product 1

HCID 21485772HCID 21485772, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 14797Potassium HydroxideSolvent

Procedure

Reflux a mixture of 6-(m-acetoxyphenyl)-1-diethylaminohexan-3-one and 6-(m-acetoxyphenyl)hex-1-en-3-one (1 g), with 2-methylcyclopentane-1,3-dione (1.5 g) in 0.12% methanolic potassium hydroxide (6 cc) for 18 hours. Remove methanol (2 cc) under reduced pressure and add chloroform (60 cc). Wash the solution in turn with dilute sulfuric acid (25 cc), saturated potassium bicarbonate solution, and brine; dry and evaporate the solvent. The product (0.8 g) is the adduct 2-(6-m-acetoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione in admixture with some of the corresponding free phenol; infrared absorption: 2.86 to 3.08 (broad low-intensity band), 5.71, 5.81, 5.85, and 8.26 μ.

Workup

  1. temperatureReflux
  2. washWash the solution in turn with dilute sulfuric acid (25 cc), saturated potassium bicarbonate solution, and brine
  3. customdry
  4. customevaporate the solvent
  5. customabsorption

Sources & evidence

ORD record
ord-8782780bea62495b8605cb452e75635c
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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