Lithium Hydroxide → 3-(4-Cyanotetrahydro-2H-pyran-4-yl)benzoic acid

HRID 1184850Notes

Reaction equation

HRID 1184850 reaction equation
[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].[OH-].[Li+]>C1COCC1.CO.O.O>[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57441036methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

Product 1

HCID 574410373-(4-Cyanotetrahydro-2H-pyran-4-yl)benzoic acidYield 42.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate 80 (1.3 g, 5.3 mmol) in (25 mL) of THF/MeOH/H2O (3/1/1) was added lithium hydroxide (419 mg, 17.5 mmol) in water (5 mL) and stirred overnight at rt. The reaction mixture was concentrated and extracted with CH2Cl2 to remove the excess of bis(2-chloroethyl)ether. The aqueous layer was then acidified with 2N HCl solution to (pH=1) and extracted with CH2Cl2. Organic layer was washed with brine and evaporated to give 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoic acid 81 (526 mg, 42%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with CH2Cl2
  3. customto remove the excess of bis(2-chloroethyl)ether
  4. extractionextracted with CH2Cl2
  5. washOrganic layer was washed with brine
  6. customevaporated

Sources & evidence

ORD record
ord-13feeef7b0a1466b8666307db0e43293
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

Loading…