Acetic Acid → 82613-32-9

HRID 1478237Notes

Reaction equation

HRID 1478237 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.CC(O)=O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])/[CH:11]=[CH:17]/[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14][CH3:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7467P-ChloroacetophenoneHCID 86582-MethoxybenzaldehydeHCID 14797Potassium Hydroxide

Product 1

HCID 534623282613-32-9Yield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (1.415 g, 25.2 mmol) was added to a solution of 1-(4-chlorophenyl)ethanone (3.9 g, 25.2 mmol) and 2-methoxybenzaldehyde (3.43 g, 25.2 mmol) in methanol (100 ml) at RT and the solution was stirred for 18 hours. The solution was concentrated under reduced pressure until a precipitate was formed. AcOH (1.444 ml, 25.2 mmol) was added and the mixture was cooled down to 0° C.-5° C. The mixture was stirred for 1 hour and the light yellow precipitate was separated by filtration and washed with cold methanol to afford 6.72 g (24.39 mmol, 97% yield) of the title compound. LCMS: (M+H)=273; tR=1.28 min (LC-MS 3). 1H-NMR (d6-DMSO, 600 MHz) δ ppm 8.12 (d, 2H) 8.04 (d, 1H) 7.98 (d, 1H) 7.86 (d, 1H) 7.62 (d, 2H) 7.45 (t, 1H) 7.10 (d, 1H) 7.02 (t, 1H) 3.88 (s, 3H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure until a precipitate
  2. customwas formed
  3. temperaturethe mixture was cooled down to 0° C.-5° C
  4. stirringThe mixture was stirred for 1 hour
  5. customthe light yellow precipitate was separated by filtration
  6. washwashed with cold methanol

Sources & evidence

ORD record
ord-fada9e3626de4864b3bcbec64f9fd4c3
Source dataset
uspto-grants-2016_08
Patent number
US09403827B2

Reaction notes

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