Methanol → HCID 57804104, compound

HRID 2102936Notes

Reaction equation

HRID 2102936 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=[C:8]([F:18])[C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+].CO>O>[CH3:15][C:14]([CH3:17])([CH3:16])[C:13]#[C:12][C:10]1[CH:9]=[C:8]([F:18])[C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57804146Methyl 4-(3,3-dimethyl-1-butyn-1-yl)-2,6-difluorobenzoate

Product 1

HCID 57804104HCID 57804104, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2,6-difluoro-4-(3,3-dimethylbut-1-ynyl)benzoate (1.0 g, 0.004 mol) and lithium hydroxide (0.57 g, 0.012 mol) were placed in a 3:1 mixture of methanol:water (60 mL) and heated at 60° C. for 3.5 h. 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 coc. HCl. A white solid crashed out which was filtered and washed thoroughly with water. The solid was dried in the vacuum oven to give the product (0.79 g, 84%) as a solid. m/z=237.1 (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 the vacuum oven

Sources & evidence

ORD record
ord-3122483c3fe2498a91eaf697677a8722
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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