Acetophenone → HCID 54143631, compound

HRID 990901Notes

Reaction equation

HRID 990901 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])[CH3:14].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[CH:14][C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 14798Sodium HydroxideHCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 54143631HCID 54143631, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(39) To a solution of 2,6-dimethoxybenzaldehyde (250 mg, 1.50 mmol) and acetophenone (180 mg, 1.50 mmol) in 2.2 ml of methanol was added 1.0 ml of 40% sodium hydroxide in water at 10° C. After stirring overnight at room temperature, a solid precipitated. The precipitate was recrystallized from methanol to afford 350 mg (87.1%) of a white, flaky solid: mp 54.9-55.8° C. (lit. mp 54-55° C., Noyce and Jorgenson, J. Am. Chem. Soc., 1963, 85, 2420-2426). 1H NMR (250 MHz) δ 8.33-8.26 (d, 1H), 8.05-7.97 (m, 3H), 7.57-7.49 (m, 3H), 7.30 (m, 1H), 6.61-6.57 (d, 2H), 3.92 (s, 6H); 13C NMR 192.3, 160.6, 139.2, 136.0, 132.4, 131.7, 128.6, 125.1, 113.1, 105.8, 103.9, 56.0 ppm.

Workup

  1. customa solid precipitated
  2. customThe precipitate was recrystallized from methanol
  3. customto afford 350 mg (87.1%) of a white, flaky solid

Sources & evidence

ORD record
ord-f59cf2edd8d74927ad1bb0cb8e5d97fc
Source dataset
uspto-grants-2002_10
Patent number
US06462075B1

Reaction notes

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