Benzyl Alcohol → [2-(Benzyloxy)-2-oxoethoxy]acetic acid

HRID 992586Notes

Reaction equation

HRID 992586 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][O:3][CH2:2]1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH2:9]([O:16][C:5]([CH2:4][O:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 8471TriethylamineHCID 782321,4-Dioxane-2,6-dione

Product 1

HCID 15221624[2-(Benzyloxy)-2-oxoethoxy]acetic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diglycolic anhydride (4.11 g, 31.9 mmol) was dissolved in methylene chloride and benzyl alcohol (3.3 g, 31.9 mmol) was added, followed by triethylamine (3.22 g, 31.9 mmol). The reaction mixture was stirred at room temperature for 4 hours. Toluene (20 mL) was added, volatiles were evaporated and the residue was dried on vacuum pump overnight to afford 7.17 g of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ4.17 (s, 2H), 4.26 (s, 2H), 5.18 (s, 2H), 7.21-7.42 (m, 5H).

Workup

  1. customvolatiles were evaporated
  2. customthe residue was dried on vacuum pump overnight

Sources & evidence

ORD record
ord-f6f35c36c17c4045a5181b8fce122529
Source dataset
uspto-grants-2002_10
Patent number
US06469065B1

Reaction notes

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