Hydrochloric Acid → 4-[4-(1-Adamantyl)-phenoxy]butyric acid

HRID 629530Notes

Reaction equation

HRID 629530 reaction equation
[C:1]12([C:11]3[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Li+].Cl>O.C1COCC1>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:24][CH:25]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54179703Ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate

Product 1

HCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acidYield 97.12%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate (1.1 g, 3.50 mmol) in H2O/THF (1 mL/1.20 mL) was added lithium hydroxide monohydrate (0.14 g, 7.00 mmol), and stirred at room temperature overnight. The reaction mixture was adjusted to acidic solution with 1 N aqueous HCl and extracted with dichloromethane. The organic layer was washed with H2O and brine, and dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give 4-(4-(adamantan-1-yl)phenoxy)butanoic acid as a white solid (0.98 g, 97.12% yield).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solvent was filtered
  5. customevaporated under reduced pressure
  6. customto afford a crude solid, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0bf01ac3921a4f40a5def06e19228002
Source dataset
uspto-grants-2016_04
Patent number
US09315507B2

Reaction notes

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