Methanol → HCID 57804228, compound

HRID 2102920Notes

Reaction equation

HRID 2102920 reaction equation
[CH3:1][C:2]1[CH:12]=[C:11]([C:13]#[C:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Li+].CO>O>[CH3:16][C:15]([CH3:18])([CH3:17])[C:14]#[C:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([OH:6])=[O:5])=[C:2]([CH3:1])[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57804232HCID 57804232, compound

Product 1

HCID 57804228HCID 57804228, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-methyl-4-(3,3-dimethylbut-1-ynyl)benzoate (4.8 g, 0.020 mol) and lithium hydroxide (2.8 g, 0.058 mol) were placed in 3:1 mixture of methanol:water (80 mL) and heated at 60° C. for 3.5 h. TLC and LCMS indicated product formation. The reaction was cooled and concentrated in vacuo to a volume of 20 mL. The mixture was placed in an ice-water bath and acidified to pH 5 with conc. HCl. A white solid crashed out which was filtered and washed thoroughly with water. The solid was dried in a vacuum oven to give the product (4.1 g, 97%) as a solid. m/z=215.1 (M−1).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo to a volume of 20 mL
  3. customThe mixture was placed in an ice-water bath
  4. filtrationwas filtered
  5. washwashed thoroughly with water
  6. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-7363292690204734bbef932243925ee9
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

Loading…