Lithium Hydroxide → 3-Cyano-4-(cyclopropylmethoxy)benzoic acid

HRID 2192480Notes

Reaction equation

HRID 2192480 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:17][CH2:16]1)[C:6]([O:8]C)=[O:7])#[N:2].[OH-].[Li+]>O1CCCC1.CO.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:16][CH2:17]1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66877477Methyl 3-cyano-4-(cyclopropylmethoxy)benzoate

Product 1

HCID 668780013-Cyano-4-(cyclopropylmethoxy)benzoic acidYield 73.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-4-[(cyclopropylmethyl)oxy]benzoate (D23; 74 mg, 0.320 mmol) was stirred at room temperature under nitrogen with lithium hydroxide (15.33 mg, 0.640 mmol) in tetrahydrofuran (THF) (2 ml), methanol (2 ml) and water (1 ml) for 20 h. The mixture was partitioned between water (20 ml), 2N hydrochloric acid (5 ml) and ethyl acetate (3×20 ml), and the organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and evaporated in vacuo to give the title compound as a white solid (51 mg)

Workup

  1. customThe mixture was partitioned between water (20 ml), 2N hydrochloric acid (5 ml) and ethyl acetate (3×20 ml)
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b585d34c52f9402b96a47613b54e061b
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…