Water → HCID 58609784, compound

HRID 408505Notes

Reaction equation

HRID 408505 reaction equation
C[O:2][C:3]([C:5]1([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Li+].O>C1COCC1>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]#[C:8][C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58609940HCID 58609940, compound

Product 1

HCID 58609784HCID 58609784, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-methoxy-phenylethynyl)-cyclopropanecarboxylic acid methyl ester (2.2 g, 9.4 mmol), lithium hydroxide (0.6 g, 14 mmol) in THF (30 mL), and water (30 mL) was stirred for 6 hours. The solution was washed with ether and the aqueous layer was acidified to pH=4 and then extracted with ether. The organic layer was dried over sodium sulfate, and evaporated to dryness to yield 1-(4-methoxy-phenylethynyl)-cyclopropanecarboxylic acid as a white solid (2.0 g, 0.0092 mmol, 98%). ESI-MS m/z calc. 216.1. found; 217.16 (M+1)+ 1H NMR (CDCl3): δ 7.35 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.8 Hz. 2H), 3.79 (s, 3H), 1.69 (m, 2H), 1.47 (m, 2H).

Workup

  1. washThe solution was washed with ether
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ca0fe7980f024055bd52c0e274d1e031
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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