Hydrochloric Acid → 1,2-Cyclopropanedicarboxylic acid, trans-

HRID 1610056Notes

Reaction equation

HRID 1610056 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]([O:11]CC)=[O:10])=[O:5])C.Cl.[Na+].[Cl-]>[OH-].[Na+]>[C@@H:7]1([C:9]([OH:11])=[O:10])[CH2:8][C@H:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 117153031,2-Diethyl (1R,2R)-1,2-cyclopropanedicarboxylate

Product 1

HCID 69504501,2-Cyclopropanedicarboxylic acid, trans-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
22 °C

Procedure

Diethyl carboxylate 3 (16.9 g, 19.3 mmol) was dissolved in 170 ml of 2N NaOH and heated under reflux for 1 h. The solution was stirred for additional 18 h at 22° C. The solution was cooled, adjusted to pH 3 with 2N HCl, saturated with NaCl, and finally extracted with ethyl acetate (2×100 ml). The pooled extracts were dried (Na2SO4), evaporated to dryness, and the white residue was used for the next step without further purification (8.5 g, 79%); mp 175-176° C. 1H-NMR (D2O): δ1.42 (m, 2H), 2.18 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe solution was cooled
  4. extractionfinally extracted with ethyl acetate (2×100 ml)
  5. dry with materialThe pooled extracts were dried (Na2SO4)
  6. customevaporated to dryness
  7. customthe white residue was used for the next step without further purification (8.5 g, 79%)

Sources & evidence

ORD record
ord-cc13c1acec874220863569fa36b9f0ec
Source dataset
uspto-grants-2006_01
Patent number
US06982351B2

Reaction notes

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