Hydrochloric Acid → HCID 54349283, compound

HRID 225117Notes

Reaction equation

HRID 225117 reaction equation
[C:1]([C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][CH2:24][N:25]([CH2:28]CO)[CH2:26][CH3:27].Cl>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CCOCC>[C:1]([C:9]1[CH:22]=[CH:21][C:12]([O:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH2:18][CH2:28][N:25]([CH2:26][CH3:27])[CH2:24][CH3:23])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7497DiethylethanolamineHCID 23328940Methyl 2-(4-benzoylphenoxy)-2-methylpropanoate

Product 1

HCID 54349283HCID 54349283, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

299 g (1 mole) of methyl 2-(p-benzoylphenoxy)-2-methylpropionate, 30 g of titanium isopropylate and 117 g (1 mole) of diethylaminoethanol are placed in a 500-cc flask. The reaction mixture is heated for 45 minutes at 120° C. (interior temperature) so as to distil off all the alcohol formed. The mixture is then allowed to cool and poured on to 10% hydrochloric acid in the presence of ether. The aqueous phase is made alkaline and then extracted with methylene chloride. The organic phase is carefully washed with water, then dried, decolorised and concentrated under vacuum. The residual oil is the desired ester. Yield 264 g, 69%. The maliate salt melts at 62° C.

Workup

  1. customto distil off all the alcohol
  2. customformed
  3. temperatureto cool
  4. extractionextracted with methylene chloride
  5. washThe organic phase is carefully washed with water
  6. customdried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-360c858a292d49a1a24a0915a19f93c8
Source dataset
uspto-grants-1980_11
Patent number
US04235896

Reaction notes

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