Lithium Hydroxide → HCID 21964124, compound

HRID 2212048Notes

Reaction equation

HRID 2212048 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:19])/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1>O.O1CCOCC1.[OH-].[Na+]>[CH:16]1([C:14]([C:11]2[CH:12]=[CH:13][C:8](/[CH:7]=[CH:6]/[C:5]([OH:19])=[O:4])=[CH:9][CH:10]=2)=[O:15])[CH2:17][CH2:18]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 1474745HCID 1474745, compound

Product 1

HCID 21964124HCID 21964124, compoundYield 83.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of lithium hydroxide (27 mg, 1.1 mmol) in water (2.00 ml) was added to a solution of (E)-3-(4-(cyclopropanecarbonyl)phenyl)acrylic acid methyl ester (217 mg, 0.94 mmol) in 1,4-dioxane (2.00 ml). 1,4-Dioxane was added until a clear solution was obtained. The reaction mixture was stirred for 16 h at room temperature. It was diluted with an 1 N aqueous solution of sodium hydroxide (50 ml) and washed with tert-butyl methyl ether (2×40 ml). The aqueous solution was acidified with a 10% aqueous solution of sodium hydrogensulphate until pH 3 was obtained. It was extracted with ethyl acetate (3×100 ml) The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo to give 170 mg of crude (E)-3-(4-(cyclopropanecarbonyl)phenyl)acrylic acid which was used in the next step without further purification.

Workup

  1. customwas obtained
  2. washwashed with tert-butyl methyl ether (2×40 ml)
  3. customwas obtained
  4. extractionIt was extracted with ethyl acetate (3×100 ml) The combined organic layers
  5. dry with materialwere dried over magnesium sulphate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-03b9dc7461574f9483cd5281c19a2449
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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