Hydrochloric Acid → HCID 66934289, compound

HRID 1879555Notes

Reaction equation

HRID 1879555 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][C:24]=1[O:31][CH2:32][O:33][CH3:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+].Cl>CCO.CCOCC>[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26](/[CH:27]=[CH:13]/[C:12]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:9][O:10][CH3:11])=[CH:7][C:2]=2[OH:1])=[O:14])=[CH:25][C:24]=1[O:31][CH2:32][O:33][CH3:34])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117455591-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanoneHCID 23076398HCID 23076398, compound

Product 1

HCID 66934289HCID 66934289, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To 1-(2-hydroxy-4-(methoxymethoxy)phenyl)ethanone (618 mg, 3.15 mmol) and 4-(benzyloxy)-3-(methoxymethoxy)benzaldehyde (816 mg, 3 mmol) in a 25-mL round-bottom flask under Ar atmosphere was added 2.5 mL of a freshly made 5% KOH in EtOH solution. The mixture was vigorously stirred at rt until it solidified and kept at rt for 6 days. It was taken up in ether (100 mL) and added 0.5 M HCl to pH=5, and stirred for 3 min. The mixture was washed with water (2×100 mL) and dried over MgSO4 and concentrated. The residue was chromatographed (hexane/EtOAc) to afford (E)-3-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-1-(2-hydroxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one as a clear oil (780 mg, 58%). MS (ESI) m/z 451 (M+H+).

Workup

  1. stirringstirred for 3 min
  2. washThe mixture was washed with water (2×100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed (hexane/EtOAc)

Sources & evidence

ORD record
ord-ab96c4e7172b40afaaf7568973a4c60e
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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