Methanol → HCID 10921701, compound

HRID 1524862Notes

Reaction equation

HRID 1524862 reaction equation
[CH2:1]([CH:8]([C:12]([OH:14])=[O:13])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:19]O>>[CH2:1]([CH:8]([C:9]([O:11][CH3:19])=[O:10])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 12031Benzylmalonic acidHCID 24386Thionyl Chloride

Product 1

HCID 10921701HCID 10921701, compoundYield 35%

Procedure

Benzyl malonic acid (19.4 g, 0.10 mol) was dissolved in 180 mL of MeOH. The mixture was cooled in an ice-bath and to it was added thionyl chloride dropwise over 30 min (7.3 mL, 0.10 mol). The mixture was stirred in the ice-bath for 30 min and then at RT for 30 min under N2. The solvent was removed, and the residue was dissolved in aqueous NaHCO3. The basic solution was extracted with EtOAc to remove the bis-ester which was discarded. The aqueous solution was then acidified with aqueous HCl to pH 5 and extracted with EtOAc. The EtOAc extract was washed with brine, dried over Na2SO4, and concentrated to give 7.2 g of 2-benzyl-3-methoxy-3-oxopropanoic acid (35%). MS 209.24 (M+H)+.

Workup

  1. temperatureThe mixture was cooled in an ice-bath and to it
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in aqueous NaHCO3
  4. extractionThe basic solution was extracted with EtOAc
  5. customto remove the bis-ester which
  6. extractionextracted with EtOAc
  7. extractionThe EtOAc extract
  8. washwas washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-728208d608df4520aca872cb09381f3e
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

Loading…