Water → 2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid

HRID 1047895Notes

Reaction equation

HRID 1047895 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([CH3:12])[C:5]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1.[OH-].[K+].O>CCO>[CH:14]1([O:13][C:5]2[C:6]([CH3:12])=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][C:4]=2[C:3]([OH:18])=[O:2])[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593140822-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid methyl ester

Product 1

HCID 593143012-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid methyl ester (410 mg, 1.64 mmol) is dissolved in EtOH (15 mL), and solid KOH (1.90 g, 32.8 mmol) and water (1.5 mL) are added. The mixture is stirred at RT for 1 h then concentrated in vacuo. The residue is dissolved in water (10 mL) and acidified with conc. HCl then extracted with EtOAc (3×10 mL). The combined organic layers are dried over anhydrous MgSO4 and concentrated in vacuo to give product (284) as viscous yellow oil (387 mg, 100%).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue is dissolved in water (10 mL)
  3. extractionthen extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layers are dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e93bfb7b7c149958716ce3e5bb9be81
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…