Dimethylformamide → 5-Chloro-2,3-dimethoxybenzaldehyde

HRID 1910648

反応式

HRID 1910648 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:13]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([O:10][CH3:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehyde

生成物 1

HCID 41722755-Chloro-2,3-dimethoxybenzaldehyde収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
61 °C

実験手順

A mixture of 5-Chloro-2-hydroxy-3-methoxybenzaldehyde (275 g, 1.47 mol) and DMF were stirred as potassium carbonate (411 g, 2.97 mol) was added over 5 minutes. The mixture temperature rose from 22 to 29° C. over 10 minutes. Dimethylsulfate (283 g, 2.24 mol) was added over 15 minutes causing a temperature rise from 28 to 47° C. The mixture was then heated with a heating mantle to 61° C. over 15 minutes and stirred at 61° C. for 1.5 hours; the reaction was complete by TLC. The reaction mixture was cooled to 22° C., transferred to a 22-L flask and diluted with water (8.2 L) over 5 minutes; the temperature rose to 38° C. The light yellow mixture was filtered and the flask and filter cake rinsed with 1.5 L water. The solid was dried under vacuum for 15 hour at 50° C. The material contained inorganic salts and was suspended in water (3 L) for 1.5 hours. After filtration and a 500 mL water rinse, the filter cake was dried under by suction and overnight at 65° C. under vacuum. Yield: 305 g (100% yield, 99.1% purity).

後処理

  1. additionwas added over 5 minutes
  2. customfrom 28 to 47° C
  3. temperatureThe reaction mixture was cooled to 22° C.
  4. customtransferred to a 22-L flask
  5. customrose to 38° C
  6. filtrationThe light yellow mixture was filtered
  7. filtrationthe flask and filter cake
  8. washrinsed with 1.5 L water
  9. customThe solid was dried under vacuum for 15 hour at 50° C
  10. waitwas suspended in water (3 L) for 1.5 hours
  11. filtrationAfter filtration
  12. washa 500 mL water rinse
  13. customthe filter cake was dried under by suction and overnight at 65° C. under vacuum

出典と根拠

ORDレコード
ord-308e9d97f34646a499d8d2895e88da88
出典データセット
uspto-grants-2013_12
特許番号
US08604021B2

関連ノート

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