1-(3-Hydroxy-4-methoxyphenyl)ethanone → HCID 25100251, compound

HRID 41936

Reaction equation

HRID 41936 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[CH3:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19][NH2:20]>>[CH3:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19]/[N:20]=[C:10](/[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=1)\[CH3:11]

Participants

3

Reactant 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 66761654HCID 66761654, compound

Product 1

HCID 25100251HCID 25100251, compoundYield 91%

Procedure

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-methylbenzyl)hydroxylamine hydrochloride (28) (57 mg, 0.328 mmol) according to the general procedure II-B defined above. After being heated for 15 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30264 (78 mg, 91%) as a pale-orange oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Workup

  1. temperatureAfter being heated for 15 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  5. washwashed with H2O (2×10 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oil thus obtained
  10. washwas subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-b6fa4720a0034f139aef0d71cd3f1cc4
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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