Sodium Hydroxide → HCID 22923629, compound

HRID 266038Notes

Reaction equation

HRID 266038 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:18])[CH2:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][C:12]([OH:17])([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2>CO>[OH:17][C:12]12[CH2:13][CH:14]3[CH2:15][CH:10]([CH2:9][CH:8]([CH:7]3[CH2:6][C:5]([OH:18])=[O:4])[CH2:16]1)[CH2:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54210579HCID 54210579, compound

Product 1

HCID 22923629HCID 22923629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 2.5 N sodium hydroxide solution 0.49 ml was added to methanol 10 ml solution of 5-hydroxy-2-adamantyl acetic acid methyl ester 181.5 mg and stirred at room temperature for 14 hours. Reaction mixture was concentrated in vacuo. Saturated sodium bicarbonate solution was added to the residue and washed with ether. Aqueous layer was adjused to pH 1 by adding 12 N hydrochloric acid, and extracted with ethyl acetate, then dried by adding anhydrous sodium sulfate. After removal of the drying agent, the filtrate was concentrated in vacuo to obtain the product as a mixture of stereoisomer. (a mixture of stereoisomer 1:1 measured by gas chromatography)

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionSaturated sodium bicarbonate solution was added to the residue
  4. washwashed with ether
  5. additionby adding 12 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customdried
  8. additionby adding anhydrous sodium sulfate
  9. customAfter removal of the drying agent
  10. concentrationthe filtrate was concentrated in vacuo
  11. customto obtain the product
  12. additionas a mixture of stereoisomer
  13. addition(a mixture of stereoisomer 1:1

Sources & evidence

ORD record
ord-8e03649b6aed4037baed3b1ff3f89219
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Reaction notes

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