Hydrochloric Acid → HCID 66882442, compound

HRID 1784029Notes

Reaction equation

HRID 1784029 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1[C:12]([O:14]CC)=[O:13])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 929224HCID 929224, compound

Product 1

HCID 66882442HCID 66882442, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 20.0 g of trans-(1SR,2SR)-4-methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester and 36.6 g of potassium carbonate in 200 ml of MeOH was heated at reflux temperature for 2 h. The mixture was cooled to 22°, diluted with 200 ml of water, the pH was adjusted to 2 using 80 ml of 25% HCl and the mixture was evaporated to half of the volume. The aqueous layer was extracted with AcOEt, the organic layer was washed with water, dried and evaporated to give 16.7 g of a crude mixture of mono and diacid. Optionally this mixture can be purified on silica using CH2Cl2/MeOH (19:1) to give 8.60 g of the pure title compound 1a. MS: 183.3 (M−H)−.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture was cooled to 22°
  4. customthe mixture was evaporated to half of the volume
  5. extractionThe aqueous layer was extracted with AcOEt
  6. washthe organic layer was washed with water
  7. customdried
  8. customevaporated
  9. customto give 16.7 g of a crude mixture of mono and diacid
  10. customOptionally this mixture can be purified on silica

Sources & evidence

ORD record
ord-bbb351fe6fd04e98bd244d8546e5d60e
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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