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Hydrochloric Acid → 6-Chloro-5-nitro-3H-isobenzofuran-1-one

HRID 1739837
ノート
印刷プレビュー

反応式

HRID 1739837 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([Cl:17])=[CH:10][C:7]=1C#N)(=[O:3])C.C1COCC1.[OH-].[Na+].Cl>CO>[Cl:17][C:11]1[CH:10]=[C:7]2[C:6]([CH2:5][O:4][C:1]2=[O:3])=[CH:13][C:12]=1[N+:14]([O-:16])=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 154289162-Acetoxymethyl-5-chloro-4-nitrobenzonitrile

生成物 1

HCID 154289176-Chloro-5-nitro-3H-isobenzofuran-1-one収率 88.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-acetoxymethyl-5-chloro-4-nitrobenzonitrile (19.5 g, 77 mmol) in MeOH:THF (600 mL, 2:1) was added a solution of 1M aqueous NaOH (100 mL, 100 mmol). After stirring at room temperature for 30 min. TLC showed no starting material remaining. The mixture was acidified with 6M aqueous HCl (100 mL, 0.6 mol), heated at 60° C. for 1 h, cooled to room temperature and stirred for 6 h. Volatile solvents were evaporated in vacuo. The residue was suspended in H2O and filtered. The solid collected was washed with H2O and dried under vacuum to give the title compound (14.5 g, 88%) as an orange-yellow solid. 1H NMR (CDCl3): δ 8.11 (s, 1H), 7.92 (s, 1H), 5.40 (s, 2H).

後処理

  1. temperatureheated at 60° C. for 1 h
  2. temperaturecooled to room temperature
  3. stirringstirred for 6 h
  4. customVolatile solvents were evaporated in vacuo
  5. filtrationfiltered
  6. customThe solid collected
  7. washwas washed with H2O
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-b9ec84dcafdd425db2fdb1c71d0da373
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968958

反応ノート

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