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

HRID 886673
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HRID 886673 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.CN(C)C=O>[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

7

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%

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 6228Dimethylformamide용매2회

실험 절차

A 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer was charged with 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, and the resulting mixture was stirred for 30 minutes at room temperature. Subsequently, 300 ml of a dimethylformamide solution containing 100 g (412 mmol) of 2-methyl-2-adamantyl chloroacetate was added gradually to the reaction mixture. The temperature was then raised to 40° C., and the reaction mixture was stirred at that temperature for 4 hours. Following completion of the reaction, 2,000 ml of diethyl ether was added, the solution was filtered, and the filtrate was washed 3 times with 500 ml samples of distilled water. Crystallization was then performed using a mixed solution of toluene (300 ml) and heptane (200 ml), yielding 78 g (yield: 67%, GC purity: 99%) of the targeted colorless solid.

후처리

  1. customA 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer
  2. additionwas added gradually to the reaction mixture
  3. temperatureThe temperature was then raised to 40° C.
  4. stirringthe reaction mixture was stirred at that temperature for 4 hours
  5. additionwas added
  6. filtrationthe solution was filtered
  7. washthe filtrate was washed 3 times with 500 ml samples of distilled water
  8. customCrystallization
  9. customyielding 78 g (yield: 67%, GC purity: 99%) of the targeted colorless solid

출처 및 근거

ORD 기록
ord-02c337226cd14e5ba2414a3f2e003b3c
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247160B2

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