Citric Acid → HCID 9861952, compound

HRID 844356Notes

Reaction equation

HRID 844356 reaction equation
[CH:1]1([C:11]2[CH:12]=[C:13]([C:17](=[O:19])[CH3:18])[CH:14]=[CH:15][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:20](OCC)(=[O:26])[C:21]([O:23]CC)=[O:22].[O-]CC.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[O:26]=[C:20]([CH2:18][C:17](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH:12]=1)[C:21]([OH:23])=[O:22]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 22613226HCID 22613226, compound

Product 1

HCID 9861952HCID 9861952, compound

Procedure

Isomer A: Into 1 mL distilled tetrahydrofuran was placed 0.046 g (0.18 mmol) of 1-[3-(1,2,3,4-tetrahydronaphthalen-1-yl)-phenyl]-ethanone (isomer A), 0.054 g (0.37 mmol) diethyl oxalate, and 0.025 g (0.37 mmol) sodium ethoxide. After stirring for 1.5 hr, excess 10% citric acid solution was added and the THF removed in vacuo. The residue was partitioned between water and ethyl acetate and extracted. The combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate, filtered, and the solvent removed in vacuo to afford the title compound which was used without further purification.

Workup

  1. distillationIsomer A: Into 1 mL distilled tetrahydrofuran
  2. customthe THF removed in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. extractionextracted
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e1a542198f2b4126a1265e4f3a047b94
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

Loading…