Lithium Hydroxide → HCID 59363833, compound

HRID 1430633Notes

Reaction equation

HRID 1430633 reaction equation
C[O:2][C:3]([C:5]1([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-]>C1COCC1.O>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59363841HCID 59363841, compound

Product 1

HCID 59363833HCID 59363833, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,4-Difluoro-phenoxy)-cyclopropanecarboxylic acid methyl ester (1.89 g, 8.28 mmol) in THF (20 ml) added a solution of LiOH (0.86 g, 20.7 mmol) in water (5 ml) was added, and mixture is stirred at r.t. for 18 h. Solvent was evaporated at reduced pressure acidified with 1N HCl (pH˜2) and extracted in ethyl acetate (70 ml) and washed with brine (2×10 ml), dried over Na2SO4 and concentrated under reduced pressure to obtain 1-(2,4-Difluoro-phenoxy)-cyclopropanecarboxylic acid (1.16 g, 66%). 1H NMR (400 MHz, CDCl3): δ 1.46 (dd, J=5.6 and 9.2 Hz, 1H), 1.71 (dd, J=5.6 and 9.2 Hz, 1H), 2.27-2.31 (m, 1H), 3.97-4.0 (m, 1H), 4.85 (t, J=5.6 Hz, 1H), 6.77-83 (m, 1H), 6.85-6.92 (m, 1H), 7.0-7.06 (m, 1H).

Workup

  1. additionwas added
  2. customSolvent was evaporated at reduced pressure
  3. extractionextracted in ethyl acetate (70 ml)
  4. washwashed with brine (2×10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67ecd9dab3d244fa95a646e474ee4025
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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