Hydrochloric Acid → HCID 54054832, compound

HRID 1735706Notes

Reaction equation

HRID 1735706 reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.[H-].[Na+].[CH3:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=1)[O:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.Cl.C1C[O:30]CC1>CO>[CH3:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=1)[O:13][C:14]1[CH:15]=[CH:17][CH:22]=[CH:21][C:20]=1[C:19]([CH2:18][C:1]([O:4][CH3:5])=[O:6])=[O:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 14970243alpha-(3-Methylphenoxy)acetophenone

Product 1

HCID 54054832HCID 54054832, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1H-NMR (CDCl3): δ=2.35 (s, 3H); 2.65 (s, 3H); 6.79-7.84 (m, 8H) ppm. b) 38.7 g (0.43 mol) of dimethyl carbonate are added to a suspension of 10.3 g (0.43 mol) of sodium hydride in 230 ml of THF and then, at 50° C., a solution of 67.2 g (0.30 mol) of 2-(3-methylphenoxy)acetophenone is added dropwise. The mixture is stirred at 50° C. for 3 hours, left to cool, 60 ml of methanol are added, and the mixture is stirred at room temperature overnight. It is acidified (pH 2) with 10 percent hydrochloric acid and extracted with MTB ether. The organic phase is washed with water, dried and concentrated. 79.5 g (93% yield) of methyl 2-(3-methylphenoxy)benzoylacetate remain as dark oil.

Workup

  1. waitleft
  2. temperatureto cool
  3. stirringthe mixture is stirred at room temperature overnight
  4. extractionextracted with MTB ether
  5. washThe organic phase is washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d57a3b5b57b415bb17c51624b307928
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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