Glycolic Acid → 2-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol

HRID 909975Notes

Reaction equation

HRID 909975 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:15][C:16]([O:18][C:19]1([CH3:29])[CH:26]2[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:28][CH:20]1[CH2:21]3)[CH2:25]2)=[O:17]>C(OCC)C.CC(C)=O.CN(C=O)C>[CH3:29][C:19]1([O:18][C:16](=[O:17])[CH2:15][O:5][C:1](=[O:4])[CH2:2][OH:3])[CH:26]2[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:28][CH:20]1[CH2:21]3)[CH2:25]2

Participants

8

Reactant 4

HCID 757Glycolic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 103320062-Methyl-2-adamantyl chloroacetate

Product 1

HCID 581059672-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanolYield 67.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

37.6 g (494 mmol) of glycolic acid, 700 mL of DMF, 86.5 g (626 mmol) of potassium carbonate, and 28.3 g (170 mmol) of potassium iodide were added to a 2 L three-neck flask equipped with a thermometer, a cooling pipe, and a stirring apparatus, and then stirred for 30 minutes at room temperature. Subsequently, a solution of 300 mL of dimethylformaldehyde with 100 g (412 mmol) of 2-methyl-2-adamantyl chloroacetate was gradually added thereto. Then, the resultant was heated at 40° C., and stirred for 4 hours. After the reaction, 2,000 mL of diethylether was added thereto and filtrated, thereby obtaining the solution (filtrate). The solution thus obtained was washed three times using 500 mL of distilled water. Thereafter, crystallization was conducted using a mixture solvent of 300 mL of toluene and 200 mL of heptane, thereby obtaining 78 g of the intended compound in the form of a colorless solid (yield: 67%, GC purity: 99%).

Workup

  1. customequipped with a thermometer
  2. temperatureThen, the resultant was heated at 40° C.
  3. stirringstirred for 4 hours
  4. additionwas added
  5. filtrationfiltrated
  6. customobtaining the solution (filtrate)
  7. customThe solution thus obtained
  8. washwas washed three times
  9. customThereafter, crystallization

Sources & evidence

ORD record
ord-80a4b0ea87fa4904bb3574ed22b5f4e2
Source dataset
uspto-grants-2011_09
Patent number
US08021823B2

Reaction notes

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