Hydrochloric Acid → HCID 86729434, compound

HRID 629533Notes

Reaction equation

HRID 629533 reaction equation
[C:1]12([C:11]3[CH:24]=[CH:23][C:14]([O:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19]C)=[O:18])=[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][C:16]([CH3:21])([CH3:22])[C:17]([OH:19])=[O:18])=[CH:23][CH:24]=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 86729433HCID 86729433, compound

Product 1

HCID 86729434HCID 86729434, compoundYield 97.5%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of methyl 2-(4-(adamantan-1-yl)phenoxy)-2-methylpropanoate (1.0 g, 3.00 mmol), prepared from step 1, in H2O/THF (1:1.20 mL) was added lithium hydroxide monohydrate (0.51 g, 12.00 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 2-(4-(adamantan-1-yl)phenoxy)-2-methylpropanoic acid as a white solid (0.92 g, 96.1% 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-c2bd96e9e33346a1b662522f45f4ac8c
Source dataset
uspto-grants-2016_04
Patent number
US09315507B2

Reaction notes

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