Sodium Hydroxide → 2-(Adamantan-2-yl)acetic acid

HRID 266037Notes

Reaction equation

HRID 266037 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:17])[CH2:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2>CO>[CH:14]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]([CH2:9]3)[CH:7]1[CH2:6][C:5]([OH:17])=[O:4])[CH2:13]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54117306Methyl 2-adamantylacetate

Product 1

HCID 8709902-(Adamantan-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 2.5 N sodium hydroxide solution 433 ml was added to methanol solution 1125 ml of 2-adamantyl acetic acid methyl ester 150 g (0.72 mol) and stirred at room temperature for 6 hours. Reaction mixture was concentrated in vacuo. Aqueous sodium bicarbonate solution was added to the residue and the mixture was washed with ether. Aqueous layer was adjusted to pH 1 by adding 12 N hydrochloric acid, extracted with ethyl acetate and dried with anhydrous sodium sulfate.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionAqueous sodium bicarbonate solution was added to the residue
  4. washthe mixture was washed with ether
  5. additionby adding 12 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-e83ba4a8905241d5b530a1f2136bebf4
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Reaction notes

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