Hydrochloric Acid → 4-Hydroxy-o-toluic acid

HRID 479741

反応式

HRID 479741 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([O:12][Si](C)(C)C)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21879730Methyl 2-methyl-4-trimethylsilyloxybenzoate

生成物 1

HCID 684754-Hydroxy-o-toluic acid収率 31.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 5.7 g methyl 2-methyl-4-trimethylsilyloxybenzoate and 2.0 g LiOH in 40 mL methanol and 10 mL water. After 2 hours at reflux the reaction was poured into 10 mL concentrated HCl and then 100 g ice. Extraction with ethyl acetate followed by concentration in vacuo gave a crude solid (70:30) product:starting material. Flash Chromatography using 50-50 ethyl acetate/hexanes as an eluent gave 1.15 g 2-methyl-4-hydroxybenzoic acid, m/e=193(M+H).

後処理

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperatureAfter 2 hours at reflux the reaction
  3. extractionExtraction with ethyl acetate
  4. concentrationfollowed by concentration in vacuo
  5. customgave a crude solid (70:30) product

出典と根拠

ORDレコード
ord-5bca532660564a6fa621317c7ac27c90
出典データセット
uspto-grants-2003_11
特許番号
US06646010B2

関連ノート

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