Hydrochloric Acid → HCID 58345621, compound

HRID 2381245Notes

Reaction equation

HRID 2381245 reaction equation
[C:1]([C:9]1[CH:19]=[C:18]([O:20]CC2C=CC=CC=2)[C:17]([O:28][CH3:29])=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.Cl>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[C:1]([C:9]1[CH:19]=[C:18]([OH:20])[C:17]([O:28][CH3:29])=[CH:16][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 58345539HCID 58345539, compound

Product 1

HCID 58345621HCID 58345621, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 2-benzoyl-4-benzyloxy-5-methoxy-benzoate (reference example 11-1) (848 mg) and dichloromethane (30 mL) was added titanium tetrachloride (0.31 mL) under room temperature. After stirring for 30 minutes, 2 mol/L hydrochloric acid and ethyl acetate were added to the mixture. The separated organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10%-100% ethyl acetate/hexane, gradient elution) to give the title compound (550 mg).

Workup

  1. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: 10%-100% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-8e81f1a9f95d4551a86e091de470eb7b
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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