Formaldehyde → Methylene bis(chloroacetate)

HRID 260626

反応式

HRID 260626 の反応式
ClC[C:3]([O:5][C:6](=[O:9])[CH2:7][Cl:8])=[O:4].[CH2:10]=[O:11].[CH2:12]([Cl:14])Cl>S(=O)(=O)(O)O>[Cl:8][CH2:7][C:6]([O:5][CH2:3][O:4][C:10](=[O:11])[CH2:12][Cl:14])=[O:9]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 10946Chloroacetic anhydride

生成物 1

HCID 86587291Methylene bis(chloroacetate)収率 57%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

Chloroacetic anhydride (12.75 g, 75 mmol), paraformaldehyde (2.25 g, 75 mmol) and conc. sulfuric acid (15 drops) are added to methylene chloride (15 ml). The mixture is stirred for 24 hrs. at 50° C. under nitrogen, whereafter the reaction mixture is extracted with saturated aqueous potassium carbonate until carbon dioxide emission ends. The organic layer is dried (MgSO4), evaporated to dryness and the residue is distilled (80° C., 0.15 mmHg) to yield 10.2 g (57%) product. 1H NMR (200 MHz, CDCl3): δ 4.1 (2×CH2Cl,s), 5.9 (CH2,s). 13C NMR (200 MHz, CDCl3): δ 41.1 (CH2Cl), 81.4 (O--CH2 --O), 166.4 (CO).

後処理

  1. extractionat 50° C. under nitrogen, whereafter the reaction mixture is extracted with saturated aqueous potassium carbonate until carbon dioxide emission
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated to dryness
  4. distillationthe residue is distilled (80° C., 0.15 mmHg)

出典と根拠

ORDレコード
ord-f4dcb4ccdada4616975d8958bd41ed1b
出典データセット
uspto-grants-1996_06
特許番号
US05529766

関連ノート

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