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

HRID 1768448Notes

Reaction equation

HRID 1768448 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): δ 1.42 (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-eafa451b143c4798beed215005a9e1bc
Source dataset
uspto-grants-2007_06
Patent number
US07235695B2

Reaction notes

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