Hydrochloric Acid → HCID 13037780, compound

HRID 1156633Notes

Reaction equation

HRID 1156633 reaction equation
[CH3:1][O-].[Na+].CCC[CH:7]([CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:22]([O:28][CH3:29])(=[O:27])[C:23]([O:25]C)=O.Cl.[CH3:31][CH2:32][O:33]CC>C1C=CC=CC=1.O>[O:25]=[C:23]([CH2:31][C:32](=[O:33])[C:19]1[CH:18]=[CH:17][C:16]([CH2:14][CH2:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:1])=[CH:21][CH:20]=1)[C:22]([O:28][CH3:29])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11120Dimethyl oxalateHCID 10942334Sodium MethoxideHCID 53440159HCID 53440159, compound

Product 1

HCID 13037780HCID 13037780, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

In 15 ml of dry benzene there was suspended 1.124 g (20.8 mMol) of sodium methoxide, and the mixture was cooled. The reaction was carried out under nitrogen. To the reaction mixture there was then added 4.92 g (20 mMol) of 4-nonylacetophenone and 2.36 g (20 mMol) of dimethyl oxalate in 25 ml of benzene. The reaction mixture was stirred at room temperature for 1 hour, and then 50 ml of ether, 16 ml of 2 N hydrochloric acid, and 4 ml of water were added, followed by stirring for an additional hour. The ether layer was separated and the aqueous layer was washed three times with 15 ml of ether. The ether layers were combined and washed five times with 10 ml of water, and three times with 10 ml of saturated sodium chloride solution. The ether layer was then dried over magnesium sulfate and evaporated, giving 6.86 g of crude product. This was crystallized from boiling petroleum ether, giving 3.45 g in the first crop, m.p. 55°-57° C.; and 1.1 g in the second crop, m.p. 52°-53.5° C. Analysis:

Workup

  1. temperaturethe mixture was cooled
  2. stirringby stirring for an additional hour
  3. customThe ether layer was separated
  4. washthe aqueous layer was washed three times with 15 ml of ether
  5. washwashed five times with 10 ml of water, and three times with 10 ml of saturated sodium chloride solution
  6. dry with materialThe ether layer was then dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-a5215a209d834c69a862d093e349ef6a
Source dataset
uspto-grants-1982_06
Patent number
US04336397

Reaction notes

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