Hydrochloric Acid → Ethyl 2-hydroxy-6-vinylbenzoate

HRID 1589988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589988
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 15008897Ethyl 2-hydroxy-6-vinylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-54034659aed0475bbcda7b9622bb1bd1
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05201937

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