Lithium hydroxide, monohydrate → cis-Cinnamic acid

HRID 2400035Notes

Reaction equation

HRID 2400035 reaction equation
[C:1]1(/[CH:7]=[CH:8]\[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1>[C:1]1(/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 6428458Methyl cinnamate, (Z)-

Product 1

HCID 5372954cis-Cinnamic acidYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (z)-3-phenylpropenoic acid, methyl ester (0.8 g, 4.9 mmol) in 20% aqueous tetrahydrofuran (5 mL) was treated with lithium hydroxide hydrate (0.42 g, 9.9 mmol) and the reaction mixture was stirred under argon at room temperature for 20 hours. It was concentrated in vacuo, diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The organic extracts were discarded and the aqueous layer was acidified to pH~3 with 1N hydrochloric acid and extracted with dichloromethane (3×100 mL). The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title B compound (0.5 g). 1H NMR (CDCl3) δ11.57 (brs, 1H), 7.48 (m, 2H), 7.25 (m, 2H), 6.94 (d, J=12.2 Hz, 1H), 5.84 (d, J=12.3 Hz, 1H).

Workup

  1. concentrationIt was concentrated in vacuo
  2. additiondiluted with water (50 mL)
  3. extractionextracted with dichloromethane (2×50 mL)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-089036ef6f5b458399d19486fbda3cec
Source dataset
uspto-grants-1995_09
Patent number
US05453421

Reaction notes

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