Citric Acid → HCID 21969266, compound

HRID 1422325Notes

Reaction equation

HRID 1422325 reaction equation
C[O:2][C:3]([C@H:5]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[OH:22])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH2:24][CH2:25][CH3:26])[CH:11]=2)[C@@H:6]1[C:27]1[CH:32]=[CH:31][C:30]2[O:33][CH2:34][O:35][C:29]=2[CH:28]=1)=[O:4].[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CO.O.COC(C)(C)C>[CH2:34]1[O:33][C:30]2[CH:31]=[CH:32][C:27]([C@H:6]3[C:7]4[C:12](=[CH:11][C:10]([O:23][CH2:24][CH2:25][CH3:26])=[CH:9][CH:8]=4)[C@@H:13]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=4[OH:22])[C@@H:5]3[C:3]([OH:4])=[O:2])=[CH:28][C:29]=2[O:35]1

Participants

8

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 11733482HCID 11733482, compound

Product 1

HCID 21969266HCID 21969266, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

Methyl-(1S,2R,3S)-1-(3,4-methylenedioxyphenyl)-3-(4-methoxy-2-hydroxyphenyl)-5-propoxyindane-2-carboxylate (0.3183 g, 0.667 mmoles) was dissolved in 2 mL of tetrahydrofuran and 4 mL of methanol. A solution of lithium hydroxide (0.1402 g, 3.34 mmoles) in 1.8 mL of water was added over a period in one portion. The reaction mixture was heated to reflux temperature while monitoring the reaction progress by HPLC. After 22 hours at reflux, HPLC analysis indicated that the reaction was complete. The reaction mixture was cooled to 25° C., then diluted with t-butyl methyl ether (5 mL). A 5% solution of citric acid (5 mL) was added and the mixture was stirred for five minutes. The layers were separated and the aqueous layer was extracted with 10 mL of t-butyl methyl ether. The combined organic layers were washed twice with water and filtered. The solution was concentrated under reduced pressure to afford the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. temperatureAfter 22 hours at reflux
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with 10 mL of t-butyl methyl ether
  6. washThe combined organic layers were washed twice with water
  7. filtrationfiltered
  8. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2de06770356b47f8b1e0694c292dd291
Source dataset
uspto-grants-2000_06
Patent number
US06080862

Reaction notes

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