Potassium Hydroxide → AKOS BB-8750

HRID 1018347Notes

Reaction equation

HRID 1018347 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2)C.[OH-].[K+]>O.C(O)C>[C:7]12([O:6][CH2:5][C:4]([OH:17])=[O:3])[CH2:16][CH:11]3[CH2:10][CH:9]([CH2:15][CH:13]([CH2:12]3)[CH2:14]1)[CH2:8]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23009658HCID 23009658, compound

Product 1

HCID 6484207AKOS BB-8750

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (adamantan-1-yloxy)-acetic acid ethyl ester (A. F. Noels et al. Tetrahedron, 1982, 38, 2733) (7.29 g, 29 mmol) and potassium hydroxide (2.60 g, 46 mmol) in water-ethanol (1:2 mixture, 180 ml) was heated at reflux for 2 h. The mixture was cooled, then concentrated in vacuum and acidified with concentrated hydrochloric acid. The resultant white precipitate was dissolved in ethyl acetate (200 ml). The solution was washed with brine (2×200 ml), dried (MgSO4) and the solvent was evaporated to afford white crystalline solid (5.85 g 92%). 1H NMR (300 MHz, CDCl3) 4.08 (2H, s), 2.20-1.58 (15H, m).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuum
  4. dissolutionThe resultant white precipitate was dissolved in ethyl acetate (200 ml)
  5. washThe solution was washed with brine (2×200 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated
  8. customto afford white crystalline solid (5.85 g 92%)

Sources & evidence

ORD record
ord-b8242c7c745f4e9a85b2415b0b629827
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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