Potassium Hydroxide → HCID 68723612, compound

HRID 1471400Notes

Reaction equation

HRID 1471400 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH2:13][CH2:12][CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[C:5]=1[C:14]([O:16]C)=[O:15].[OH-].[Na+]>CCO>[CH2:3]=[C:4]1[CH2:13][CH2:12][CH2:11][C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:5]1[C:14]([OH:16])=[O:15].[CH3:3][C:4]1[CH:5]([C:14]([OH:16])=[O:15])[C:6]2([CH2:11][CH2:12][CH:13]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 68726408HCID 68726408, compound

Product 2

HCID 68723051HCID 68723051, compoundYield 4%HCID 68723612HCID 68723612, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of KOH (47.5 g, 0.72 mol) in EtOH (200 ml) was treated with methyl 7-methylspiro[4.5]dec-6-ene-6-carboxylate (15 g, 0.072 mol, prepared as described in Example 26) and the resulting mixture was stirred at reflux for 6 h, poured into cold 2N aqueous NaOH (300 ml), and extracted twice with cyclohexane (100 ml). The combined organic phases were washed with 2N aqueous NaOH (100 ml), and the combined aqueous phases were acidified with conc. HCl, and extracted twice with MTBE (150 ml). The combined organic phases were washed with water (100 ml), with a saturated aqueous solution of NaCl (150 ml), dried (MgSO4), and concentrated. FC (90 g SiO2, hexane/MTBE 88:12) of the crude product (12.8 g) gave 7-methylenespiro[4.5]decane-6-carboxylic acid (0.7 g, 5%) and 7-methylspiro[4.5]dec-7-ene-6-carboxylic acid (0.57 g, 4%).

Workup

  1. temperatureat reflux for 6 h
  2. extractionextracted twice with cyclohexane (100 ml)
  3. washThe combined organic phases were washed with 2N aqueous NaOH (100 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 (150 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c68835c300c34169bbbce4b06e8fd4a4
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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