Neopentyl glycol → HCID 58294023, compound

HRID 416027Notes

Reaction equation

HRID 416027 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH2:13][CH2:14][Br:15])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:16][C:17]([CH2:21]O)([CH2:19][OH:20])[CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([O:12][CH2:13][CH2:14][Br:15])=[C:4]([C:9]2([CH3:10])[O:20][CH2:19][C:17]([CH3:21])([CH3:18])[CH2:16][O:11]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 31344Neopentyl glycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58294044HCID 58294044, compound

Product 1

HCID 58294023HCID 58294023, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3′-bromo-2′-(2-bromoethoxy)-5′-chloroacetophenone (Reference compound No. 4-1, 4.4 g, 10 mmol), neopentylglycol (1.2 g, 1.2 mmol) and p-toluenesulfonic acid monohydrate (0.22 g, 12 mmol) in anhydrous toluene (50 mL) was refluxed overnight. After cooling, ethyl acetate (50 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL) were added to the reaction mixture and the whole was partitioned. The organic layer was washed with brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give the title reference compound (2.8 g) as a pale yellow oil (Yield 63%).

Workup

  1. temperatureAfter cooling
  2. customthe whole was partitioned
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1e722cd6cb864abaadc7dd172d27a866
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

Loading…