4'-Hydroxyacetophenone → HCID 97793, compound

HRID 1157971Notes

Reaction equation

HRID 1157971 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+]>CO>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 97793HCID 97793, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well-stirred solution of 4-hydroxy acetophenone, 1 (10 g, 73.5 mmol) and 4-methoxy benzaldehyde, 4 (8.9 mL, 73.5 mmol) in methanol (140 mL) was added 50% w/v aqueous sodium hydroxide solution (70 mL). The reaction mixture was stirred at room temperature for 12 h and then evaporated in vacuo. Water was added and acidified with hydrochloric acid (1N) and extracted with ethyl acetate. The organic layer was separated, washed with water, dried over sodium sulphate, filtered and evaporated in vacuo. The residue yielded pure 7 after purification by column chromatography. Yield 16.8 g (90%); mp 184-185° C. MS (EI) m/z 254 (M+, 100%), 253 (34.7%), 239 (32.3%), 161 (36.8%), 121 (79.5%); IR (KBr) 3371, 1654; 1H NMR (200 MHz, CDCl3) δ 7.99 (d, J=8.6 Hz, 2H), 7.78 (d, J=15.6 Hz, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.93 (d, J=7.2 Hz, 4H), 5.85 (s, 1H), 3.86 (s, 3H).

Workup

  1. customevaporated in vacuo
  2. additionWater was added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue yielded pure 7
  10. customafter purification by column chromatography

Sources & evidence

ORD record
ord-80656075132a4f398a172559e79d2929
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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