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

HRID 909975
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HRID 909975 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone
용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-80a4b0ea87fa4904bb3574ed22b5f4e2
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08021823B2

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