Potassium Hydroxide → 2,4-Bis-allyloxy-5-isopropylbenzoic acid

HRID 389963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389963
[OH-].[K+].[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10])[CH:4]=[CH2:5]>CO.O>[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([OH:11])=[O:10])[CH:4]=[CH2:5]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 58236457Methyl 2,4-bis-allyloxy-5-isopropylbenzoate

Produkt 1

HCID 582364592,4-Bis-allyloxy-5-isopropylbenzoic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Aqueous potassium hydroxide (50% w/v, 0.5 ml) was added to a mixture of methyl 2,4-bis-allyloxy-5-isopropylbenzoate (450 mg, 1.55 mmol) in methanol (6 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford 2,4-bis-allyloxy-5-isopropylbenzoic acid (418 mg, 98%) as an off-white solid. 1H NMR (DMSO-d6) 12.16 (1H, br s), 7.58 (1H, s), 6.66 (1H, s), 6.07 (2H, m), 5.51 (1H, dm), 5.44 (1H, dm), 5.28 (2H, m), 4.68 (2H, m), 4.64 (2H, m), 3.17 (1H, m), 1.15 (6H, d). MS: [M+Na]+ 299.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×10 ml)
  6. customsucked dry under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a575f892e154cde8861d01c1666077f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383619B2

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