Citric Acid → HCID 10037734, compound

HRID 2297093Notes

Reaction equation

HRID 2297093 reaction equation
[OH-:1].[Li+].Cl.[C:4](O)(=O)[CH2:5][C:6]([CH2:11][C:12](O)=O)([C:8]([OH:10])=[O:9])O.[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>>[C:6]([O:10][C:8]([C:6]1[CH:5]=[CH:4][C:18]([CH2:19][CH2:20][C:21]([OH:17])=[O:1])=[CH:12][CH:11]=1)=[O:9])([CH3:11])([CH3:8])[CH3:5]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028Tetrahydrofuran

Product 1

HCID 10037734HCID 10037734, compound

Procedure

The product of Ex. A-23, Part F, (14 g, 55.5 mM) was dissolved in 90 mL of tetrahydrofuran. 1N Lithium hydroxide (90 ml) was added and the reaction stirred at room temperature for 20 min. The reaction mixture was poured into 200 mL of 1:1 mixture of 1N HCl and saturated citric acid, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated to yield a white solid (13 g 100%). 1H NMR (CDCl3) δ 1.59 (s, 9H), 2.70 (t, J=7 Hz, 2H), 3.00 (t, J=7 Hz, 2H), 7.24 (d, J=8 Hz, 2H), 7.90, (d, J=8 Hz, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a white solid (13 g 100%)

Sources & evidence

ORD record
ord-f0ae9ca526d1443084e50dd9995d660a
Source dataset
uspto-grants-2002_12
Patent number
US06489333B2

Reaction notes

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