Hydrochloric Acid → 2-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid

HRID 1517535Notes

Reaction equation

HRID 1517535 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:5]=1[C:16]1[C:17]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:18][CH:19]=[CH:20][CH:21]=1.C1COCC1.[OH-].[Na+].Cl>CO.O>[CH2:23]([O:22][C:17]1[C:16]([C:5]2[CH:6]=[C:7]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:8]([O:10][CH3:11])=[CH:9][C:4]=2[C:3]([OH:30])=[O:2])=[CH:21][CH:20]=[CH:19][N:18]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 673789942-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid methyl ester

Product 1

HCID 673744112-(2-Benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

step 3—To a suspension of 66 (960 mg, 2.36 mmol) in MeOH (15 mL), H2O (10 mL), and THF (10 mL) was added NaOH (1.00 g, 23.6 mmol). The reaction mixture was heated at 70° C. overnight and gradually became homogeneous. The mixture was cooled to 0° C., acidified to pH 3 with 1.0 M aq HCl and thrice extracted with EtOAc. The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 895 mg (97%) of 2-(2-benzyloxypyridin-3-yl)-4-tert-butyl-5-methoxybenzoic acid (68) as a beige solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-897d4275b64940e5beef43f4bd3e5eb1
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

Loading…