Hydrochloric Acid → Flavanone

HRID 1844232Notes

Reaction equation

HRID 1844232 reaction equation
Cl.[C:2]1([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[OH:19]>>[O:11]1[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:8](=[O:19])[CH2:9][CH:10]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7189Cinnamoylbenzene

Product 1

HCID 10251Flavanone

Procedure

General procedure C for deprotection of the MOM group from chalcones to synthesize 7b, 7d, 7f. Concd HCl (0.25 mL/MOM group) was added to a solution of chalcone (1 mmol) in methanol (10 mL) at room temperature and the reaction mixture was stirred for 24-36 h until disappearance of starting material. The solvent was evaporated under reduced pressure and the residue was column chromatographed eluting with 25% ethyl acetate in hexanes to afford flavanone in high yield.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customchromatographed
  3. washeluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ec5181bdc4e246928005b77bbca73689
Source dataset
uspto-grants-2015_02
Patent number
US08946287B2

Reaction notes

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