Hydrochloric Acid → 3-(1-Adamantyl)-4-methoxybenzoic acid

HRID 710363

Reaktionsgleichung

Reaktionsgleichung von HRID 710363
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)[CH:5]=1.[OH-].[Na+].CCO.Cl>C1COCC1.O.CCOC(C)=O>[C:12]12([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[O:10][CH3:11])[C:3]([OH:22])=[O:2])[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 14549070Methyl 3-(1-adamantyl)-4-methoxybenzoate

Produkt 1

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acidAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl-3-(1-adamantyl)-4-methoxybenzoate (0.27 g, 0.85 mmol) in THF (30 ml) was added a solution of NaOH (0.04 g) in H2O (1 ml), followed by the addition of EtOH (2 ml). The mixture was refluxed for 4 h, then cooled to room temperature and acidified with 1M HCl solution. The crude product was taken in EtOAc (100 ml) and the organic layer was washed with H2O, and dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title product (0.22 g, 85%) as colourless solid. 1H-NMR (CDCl3) 1.77 (s, 6H), 2.03 (s, 3H), 2.09 (s, 6H), 3.89 (s, 3H), 6.88 (d, 1H, J=8.44 Hz), 7.93-7.98 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 4 h
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fac5522abc9d48c5ac8fac7b3344b96f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181182B2

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