Hydrochloric Acid → 2-Chloro-6-ethylbenzoic acid

HRID 491002ノート

反応式

HRID 491002 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].CN(C)C1C=CC=CC=1.Cl.S(=O)(=O)(O)N.[C:35]([O:38]C(=O)C)(=[O:37])C.C(Cl)(Cl)Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:3]=1[C:35]([OH:38])=[O:37]

参加物

10

反応物 8

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 138791952-Chloro-6-ethylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 226137692-Chloro-6-ethylbenzoic acid

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
11 °C

実験手順

3.60 g (21.2 mmol) of 2-chloro-6-ethylaniline in 24 ml of acetic acid are introduced into a reaction vessel and the clear, colourless solution is cooled to 11° C. At that temperature, 3.25 g (31.8 mmol) of sulfuric acid (96%) are added and then, in the course of 15 minutes, 3.64 g (22.7 mmol) of a 43% aqueous sodium nitrite solution are added. The resulting dark-red solution is then stirred for 30 minutes. When a diazo colour test, e.g. using dimethylaniline-coated indicator paper, is positive and a colour spot test, e.g. using KI indicator paper moistened with aqueous 1N hydrochloric acid solution, is negative, 15 mg of sulfamic acid are added and then, at a temperature of 10° C., 8.7 ml (91.6 mmol) of acetic anhydride are added. The reaction mixture is then transferred to a glass autoclave and rinsed with 6 ml of acetic acid. At a temperature of 20° C. the autoclave is flushed out three times with nitrogen and then three times with CO. 220 mg of Pd2(dba)3.CHCl3 (0.212 mmol) in 3 ml of acetic acid are metered in using a cannula at a CO pressure of 1 bar, then a CO pressure of 8 bar is applied and the reaction mixture is stirred for 5 hours at 45° C.

後処理

  1. washrinsed with 6 ml of acetic acid
  2. customAt a temperature of 20° C. the autoclave is flushed out three times with nitrogen
  3. stirringthe reaction mixture is stirred for 5 hours at 45° C.

出典と根拠

ORDレコード
ord-ca917d3bcc564b71a0771106fc662359
出典データセット
uspto-grants-2009_05
特許番号
US07528266B2

反応ノート

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