Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid

HRID 610315

Reaktionsgleichung

Reaktionsgleichung von HRID 610315
[OH:1][CH:2]1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[Li+].[OH-].Cl>C1COCC1.CO.CCOCC.CCOC(C)=O>[OH:1][CH:2]1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)[CH:5]=[CH:4][C:3]1=2

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15391671Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate2×

Produkt 1

HCID 183145914-[(5,6,7,8-Tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 21584169Diethylether ethylacetateLösungsmittel

Versuchsvorschrift

110 mg (0.31 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in a mixture of THF and methanol was refluxed with 1 ml (1 mmol) of LiOH (1M aqueous solution). Thereafter the mixture was diluted with Et2O:EtOAc (1:1), and acidified with aqueous HCl to pH 5. The organic phase was separated, washed (water and brine), dried (MgSO4) to yield the title compound.

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed (water and brine)
  3. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-238680ad6c1f4fd8aa601d5ddbff7685
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998471

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