Hydrochloric Acid → HCID 12085578, compound

HRID 1826626Notes

Reaction equation

HRID 1826626 reaction equation
[CH2:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]COC)=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].Cl>C(O)C>[CH2:1]([O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[O:10])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12085577HCID 12085577, compound

Product 1

HCID 12085578HCID 12085578, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-allyloxy-2′-(methoxymethyloxy)benzophenone (1.1 g) in ethanol (15 mL) was added concentrated hydrochloric acid (0.96 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1) to give 4-allyloxy-2′-hydroxybenzophenone (0.87 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-2eac0a33d496464788107837e70d2d88
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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