Methanol → HCID 59314362, compound

HRID 1047911Notes

Reaction equation

HRID 1047911 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[O:12][CH:13]1[CH2:16][CH2:15][CH2:14]1.O1CCOCC1.CO.[Li+].[OH-]>CO.C(Cl)Cl.O>[Br:10][C:8]1[CH:7]=[C:6]([CH3:11])[C:5]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16]2)=[C:4]([CH:9]=1)[C:3]([OH:17])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 59314255HCID 59314255, compound

Product 1

HCID 59314362HCID 59314362, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A 100 mL flask containing 5-bromo-2-cyclobutoxy-3-methyl-benzoic acid methyl ester (2.07 g, 7.25 mmol) as prepared above is charged with 1,4-dioxane (12 mL) and MeOH (12 mL). A stirring bar is added and stirring is initiated. After dissolution, water (6 mL) is added followed by the LiOH (768 mg, 18.3 μmol). After 18 h, tlc analysis (silica, 10% MeOH/DCM) indicates that the starting material is completely consumed. The pH of the reaction mixture is carefully adjusted to pH 2 by slowly adding dilute aqueous HCl (3%, ˜11 mL). The contents of the flask are poured into a separatory funnel which contains EtOAc (50 mL). The layers are separated. The aqueous layer is extracted with EtOAc (40 mL). The combined organic phases are washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated by pumping to constant weight to give a white solid (1.82 g, 88%).

Workup

  1. customas prepared
  2. additionA stirring bar is added
  3. additionis added
  4. customis completely consumed
  5. additionby slowly adding dilute aqueous HCl (3%, ˜11 mL)
  6. additionThe contents of the flask are poured into a separatory funnel which
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (40 mL)
  9. washThe combined organic phases are washed with water (40 mL) and brine (40 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-548bf8d4e9964f28b8300862a8ab6a5c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…