Potassium Hydroxide → 2,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

HRID 41381

Reaktionsgleichung

Reaktionsgleichung von HRID 41381
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]([CH3:29])=[CH2:28])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C:27]([CH3:29])=[CH2:28])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 11955870Methyl 2,4-bis-benzyloxy-5-isopropenylbenzoate

Produkt 1

HCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl 2,4-bis-benzyloxy-5-isopropenyl-benzoate (700 mg, 1.80 mmol) was dissolved in methanol (20 ml), a solution of potassium hydroxide (286 mg, 5.1 mmol) in water (4 ml) was added and the mixture was stirred and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid. The mixture was extracted with dichloromethane, the organic layer was separated and the solvent removed in vacuo to afford 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (600 mg, 89%) as a colourless solid. 1H NMR (DMSO-d6) 7.52 (2H, d), 7.47-7.29 (9H, m), 6.82 (1H, s), 5.20 (2H, s), 5.17 (2H, s), 5.06 (1H, s), 5.04 (1H, s), 2.03 (3H, s). MS: [M+H]+ 375.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. additionthe mixture acidified to pH 2 or below by the addition of 2M hydrochloric acid
  5. extractionThe mixture was extracted with dichloromethane
  6. customthe organic layer was separated
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f6a997f9f94c41c6b4ed0121655445b4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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