Lithium Hydroxide → 3-tert-Butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoic acid

HRID 217750Notes

Reaction equation

HRID 217750 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:14]=1)[C:8]([O:10]C)=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].C(Cl)Cl>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH:14]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 58136886Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoate

Product 1

HCID 581368323-tert-Butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoate (O5.059; 5.37 g) was dissolved in methanol (80 ml) and THF (160 ml), and lithiumhydroxide solution (61.28 ml, 1 M in water) was added. After stirring at 40° C. for 2 h, the mixture was dried, and the residue was taken up with water and freeze-dried. The product obtained was stirred with DCM, filtered and dried. 4.9 g of product were obtained.

Workup

  1. customthe mixture was dried
  2. customfreeze-dried
  3. customThe product obtained
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-20c114ac658d45abb1e0df8a7e5b8d85
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

Loading…