Lithium hydroxide, monohydrate → 1-(3-(Hydroxymethyl)-4-methoxyphenyl)cyclopropanecarboxylic acid

HRID 1908355Notes

Reaction equation

HRID 1908355 reaction equation
C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16](C)(C)[O:17][SiH2]C(C)(C)C)[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].O[Li].O>CO.O>[OH:17][CH2:16][C:10]1[CH:9]=[C:8]([C:5]2([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131727845HCID 131727845, compound

Product 1

HCID 591291971-(3-(Hydroxymethyl)-4-methoxyphenyl)cyclopropanecarboxylic acidYield 132.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-phenyl]-cyclopropane carboxylic acid methyl ester (6.2 g, 18 mmol) in MeOH (75 mL) was added a solution of LiOH.H2O (1.5 g, 36 mmol) in water (10 mL) at 0° C. The reaction mixture was stirred overnight at 40° C. MeOH was removed by evaporation under vacuum. AcOH (1 mol/L, 40 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to provide 1-(3-hydroxymethyl-4-methoxy-phenyl)-cyclopropanecarboxylic acid (5.3 g).

Workup

  1. customMeOH was removed by evaporation under vacuum
  2. additionAcOH (1 mol/L, 40 mL) and EtOAc (200 mL) were added
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-0ca5aec4bee94aa8bef6631d012a1ffb
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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