Hydrochloric Acid → Methyl 3-[2-(2-methylbenzyloxy)-phenyl]-3-oxopropionate

HRID 1195919Notes

Reaction equation

HRID 1195919 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][C:10]1[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=1[CH2:12][O:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.Cl.C([O:30]CC)C>O.CO>[CH3:9][C:10]1[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=1[CH2:12][O:13][C:14]1[CH:15]=[CH:17][CH:22]=[CH:21][C:20]=1[C:19](=[O:30])[CH2:18][C:3]([O:6][CH3:7])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 538898952-(2-Methylbenzyloxy)-acetophenone

Product 1

HCID 14839838Methyl 3-[2-(2-methylbenzyloxy)-phenyl]-3-oxopropionate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

14 g (0.6 mol) of 100% pure sodium hydride and 54 g (0.6 mol) of dimethyl carbonate in 225 ml of absolute diethyl ether are initially taken under nitrogen. 72 g (0.3 mol) of 2-(2-methylbenzyloxy)-acetophenone, dissolved in 300 ml of absolute ether, are added dropwise at 20°-35° C. and the mixture is refluxed for 5 h. At 10° C., first 45 ml of methanol and then 100 ml of H2O are slowly added dropwise. The pH is then brought to 7 with dilute hydrochloric acid. The organic phase is washed several times with H2O, dried over sodium sulfate and evaporated down. The product is obtained in quantitative yield as crystals (mp.=38°-42° C.).

Workup

  1. additionare added dropwise at 20°-35° C.
  2. temperaturethe mixture is refluxed for 5 h
  3. washThe organic phase is washed several times with H2O
  4. dry with materialdried over sodium sulfate
  5. customevaporated down

Sources & evidence

ORD record
ord-1257f2c9d62a41aa9ba4b1c5473873d9
Source dataset
uspto-grants-1992_05
Patent number
US05112862

Reaction notes

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