Sodium Hydroxide → (6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acid

HRID 1420795Notes

Reaction equation

HRID 1420795 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH:7]1[CH2:12][CH:11]2[CH2:13][CH:9]([C:10]2([CH3:15])[CH3:14])[C:8]1=[CH2:16])C.[OH-].[Na+]>C(O)C>[CH3:14][C:10]1([CH3:15])[CH:9]2[CH2:13][CH:11]1[CH2:12][CH:7]([CH2:6][CH2:5][C:4]([OH:17])=[O:3])[C:8]2=[CH2:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54256708(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acid ethyl ester

Product 1

HCID 18782802(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acidYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(6,6-Dimethyl-2-methylene-bicyclo[3.1.1]hept-3-ylmethyl)-acetic acid ethyl ester (3.25 g, 14.6 mmol) was dissolved in absolute ethanol (50 ml). To this solution was added 1.0 N NaOH (20 ml). After stirring for 18 hours at ambient temperature, the reaction was then concentrated to 20 ml and partitioned between 0.1 N HCl and CH2Cl2. The CH2Cl2 layer was dried over MgSO4, filtered and concentrated under vacuum to give 2.79 g of the titled compound: C.I. m/z 195.1 [M+1]; 1H NMR (CDCl3)δ 4.78 (s, 1H), 4.77 (s, 1H), 3.02 (s, 1H), 2.75 (dd, J=4.9, 15.3 Hz, 1H), 2.56 (d, J=10.9 Hz, 1H), 2.49 (t, J=6.1 Hz, 1H), 2.38 (m, 1H), 2.24 (dt, 2.1, 12.0 Hz, 1H), 2.02 (m, 1H), 1.57 (dt, J=3.2,14.0 Hz, 1H), 1.26 (s, 3H), 1.19 (d, J=10.1,1H), 0.77 (s, 3H).

Workup

  1. concentrationthe reaction was then concentrated to 20 ml
  2. custompartitioned between 0.1 N HCl and CH2Cl2
  3. dry with materialThe CH2Cl2 layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a8928b16b4d14d7e9e3de105062be0ac
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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