Hydrochloric Acid → HCID 117724717, compound

HRID 628536Notes

Reaction equation

HRID 628536 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][C:6]=1[CH3:14])([CH3:3])[CH3:2].O1CCCC1.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23].Cl>C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.O.C(O)C>[CH2:22]([O:21][C:20](=[O:24])[CH2:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH3:14])[CH:7]=1)=[O:13])[CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 8028TetrahydrofuranHCID 20192689HCID 20192689, compound

Product 1

HCID 117724717HCID 117724717, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 26541Dibenzo-18-crown-6CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

At room temperature, to a mixture of 1-(4-isopropoxy-3-methyl-phenyl)-ethanone (described in Reference Preparation example 93) 9.4 g and tetrahydrofuran 150 ml was added diethyl carbonate 11.6 g, 55% sodium hydride 4.5 g, dibenzo-18-crown-6 0.04 g and ethanol 3 mL, and the resulting mixture was stirred with heating under reflux for nine hours. To the reaction mixture was added water, and the resulting mixture was acidified with 10% aqueous hydrochloric acid solution and was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-isopropoxy-3-methyl-phenyl)-3-oxo-propionic acid ethyl ester 12.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for nine hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b289c7a3fa4423ea2d06ee5721678f4
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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