Hydrochloric Acid → HCID 20277058、化合物

HRID 647046ノート

反応式

HRID 647046 の反応式
[CH3:1][C:2]1[C:3](=[O:19])[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].[CH:20](=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)O.Cl>C(Cl)(=O)C(Cl)=O.C1C=CC=CC=1.N1C=CC=CC=1.O>[CH3:1][C:2]1[C:3](=[O:19])[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:27]2[CH:26]=[CH:25][CH:24]=[CH:22][C:21]=2[CH:20]=[O:28])=[O:17])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

参加物

8

反応物 3

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 129061502,3,5-Trimethyl-6-(5'-carboxypentyl)-1,4-benzoquinone

生成物 1

HCID 20277058HCID 20277058、化合物

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 65578Oxalyl chloride溶媒

実験手順

The acid chloride (1.01 part) synthesized from 2,3,5-trimethyl-6-(5'-carboxypentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the free form) (1 part) and oxalyl chloride (5 volume parts) was dissolved in anhydrous benzene (10 volume parts) and the solution was added dropwise to a solution of salicylaldehyde (0.6 part) in pyridine (10 volume parts) at 25° C. After stirring for 2.5 hours, the reaction mixture was diluted with cold water (300 volume parts) and rendered acidic with dilute hydrochloric acid. It was then extracted twice with diethyl ether (300 volume parts). The extracts were pooled, washed with water and dried. The solvent was then distilled off under reduced pressure and the residue was subjected to column chromatography on silica gel. Elution with chloroform provided a yellow oil of 2,3,5-trimethyl-6-(5'-(o-formylphenyloxycarbonyl)pentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the form of o-formylphenolate) (1.3 part). To a cooled, stirred solution of this product (1.1 part) in acetone (25 volume parts) was added standard Jones reagent (2 volume parts). The solution was stirred for 100 minutes, after which it was diluted with cold water (500 volume parts), followed by extraction with ethyl acetate (500 volume parts). The extract was washed with water and dried. The solvent was then distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (50 parts). The procedure provided a yellow oil of 2,3,5-trimethyl-6-(5'-(o-carboxyphenyloxycarbonyl)pentyl)-1,4-benzoquinone (formula I-2 wherein R=H3C, n=4, in the form of o-carboxyphenolate (1.1 part).

後処理

  1. extractionIt was then extracted twice with diethyl ether (300 volume parts)
  2. washwashed with water
  3. customdried
  4. distillationThe solvent was then distilled off under reduced pressure
  5. washElution with chloroform

出典と根拠

ORDレコード
ord-2a5e189fd5c9486aada28a9e7a8345f8
出典データセット
uspto-grants-1983_10
特許番号
US04407757

反応ノート

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