Benzyl Alcohol → 3-(Benzyloxy)-3-oxopropanoic acid

HRID 129871Notes

Reaction equation

HRID 129871 reaction equation
C[C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.C(O)[C:12]1[CH:17]=[CH:16]C=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:2]([O:7][C:6](=[O:8])[CH2:5][C:4]([OH:3])=[O:9])[C:10]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 10340Sodium CarbonateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 1816593-(Benzyloxy)-3-oxopropanoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (25 g, 174 mmol) and benzyl alcohol (36 mL, 347 mmol) in toluene (100 mL) was heated at 106° C. for 24 h. The solution was poured into 5% Na2CO3 (aqueous), the organic layer was separated, and the aqueous layer was washed with ether (3×). The aqueous layer was then acidified with 1N HCl and extracted with ethyl acetate (2×). The combined ethyl acetate extracts were dried over anhydrous MgSO4, filtered and evaporated at reduced pressure to give malonic acid monobenzyl ester (11.42 g, 34%).

Workup

  1. customthe organic layer was separated
  2. washthe aqueous layer was washed with ether (3×)
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined ethyl acetate extracts were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-7e207fe3d17748a5a93ca9ad6185f0d7
Source dataset
uspto-grants-1995_11
Patent number
US05470849

Reaction notes

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