Potassium Hydroxide → HCID 68772153, compound

HRID 1471392Notes

Reaction equation

HRID 1471392 reaction equation
[OH:1][C@@H:2]1[CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([C:12]([O:14]CC)=[O:13])[C:4]([CH3:17])=[CH:3]1.[OH-].[K+].[OH-].[Na+]>C(O)C>[OH:1][C@@H:2]1[CH2:11][C:6]2([CH2:7][CH2:8][CH2:9][CH2:10]2)[C@@H:5]([C:12]([OH:14])=[O:13])[C:4]([CH3:17])=[CH:3]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 131732744HCID 131732744, compound

Product 1

HCID 68772153HCID 68772153, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 33:67 cis-/trans-ethyl 9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate (38 g, 0.16 mol, prepared as described in Example 16) was added to a solution of KOH (52.6 g, 0.8 mol) in ethanol (300 ml). The resulting mixture was stirred for 2 h at reflux, poured into cold 2N aqueous NaOH (100 ml), and extracted twice with MTBE (100 ml). The combined organic phases were washed with 2N aqueous NaOH (50 ml), the combined aqueous phases were acidified with conc. HCl, extracted twice with MTBE (150 ml), and the combined organic phases were washed with water (100 ml), with a saturated aqueous solution of NaCl (100 ml), dried (MgSO4), and concentrated, giving crude trans-9-hydroxy-7-methylspiro[4.5]dec-7-ene-6-carboxylic acid (22.7 g).

Workup

  1. temperatureat reflux
  2. extractionextracted twice with MTBE (100 ml)
  3. washThe combined organic phases were washed with 2N aqueous NaOH (50 ml)
  4. extractionextracted twice with MTBE (150 ml)
  5. washthe combined organic phases were washed with water (100 ml), with a saturated aqueous solution of NaCl (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de35ec2acdd641c2aef3c9e38050f35c
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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