Hydrochloric Acid → 3-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acid

HRID 1912110Notes

Reaction equation

HRID 1912110 reaction equation
[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH:4]1[CH2:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5]1.O1CCCC1.Cl>[Zn].O>[CH3:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH:4]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 866750383-(2,2-Dimethylpropyl)-1-cyclobutene-1-carboxylic acid

Product 1

HCID 866750393-(2,2-Dimethylpropyl)cyclobutane-1-carboxylic acidYield 114.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3-(2,2-dimethylpropyl)-1-cyclobutenecarboxylic acid (10 g), tetrahydrofuran (100 mL) and 6 N hydrochloric acid (100 mL) were mixed. To the mixture was added zinc (30 g) at ice temperature. The mixture was stirred at 70° C. overnight. After an addition of 6 N hydrochloric acid and water the mixture was filtered. The filtrate was extracted with ethyl acetate (150 mL, 100 mL). The organic layer was washed with brine (100 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (11.6 g) as a crude product.

Workup

  1. filtrationwas filtered
  2. extractionThe filtrate was extracted with ethyl acetate (150 mL, 100 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-08e3551479fb405fbb1458f518e60613
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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