Hydrochloric Acid → Ethyl 2-hydroxy-6-vinylbenzoate

HRID 1589988ノート

反応式

HRID 1589988 の反応式
[C:1](=O)([O-])[O-].[Na+].[Na+].[Br-].C([O:11][C:12]1[C:13]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:14]([CH:35]=[CH:36][CH:37]=1)[CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=O)C.C=O.Cl>O>[OH:11][C:12]1[CH:37]=[CH:36][CH:35]=[C:14]([CH:15]=[CH2:1])[C:13]=1[C:38]([O:40][CH2:41][CH3:42])=[O:39]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 10929793(3-Acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide

生成物 1

HCID 15008897Ethyl 2-hydroxy-6-vinylbenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

A solution of 12.7 g of sodium carbonate in 115 ml of water was added dropwise, while stirring vigorously at room temperature, to 33.8 g of (3-acetoxy-2-ethoxycarbonylbenzyl) triphenylphosphonium bromide (e.g. Eicher et al. Synthesis (1988) 525) in 264 ml of 36.5% by weight aqueous formaldehyde solution. The reaction mixture was stirred at 55° C. for 6 h and then poured into ice-water at pH 1 (hydrochloric acid) and extracted with ethyl acetate, after which the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Further purification was carried out by chromatography on silica gel with toluene/ethyl acetate (20:1) as eluent.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialafter which the combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customFurther purification

出典と根拠

ORDレコード
ord-54034659aed0475bbcda7b9622bb1bd1
出典データセット
uspto-grants-1993_04
特許番号
US05201937

反応ノート

読み込み中…