Hydrochloric Acid → HCID 12085578, compound

HRID 1982816Notes

Reaction equation

HRID 1982816 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 concentrated hydrochloric acid (0.96 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1) to give 4-allyloxy-2′-hydroxy-benzophenone (0.87 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added a saturated aqueous sodium hydrogen carbonate solution
  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 residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-a8206dc040ae4b4e8d5b58b6b120747e
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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