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

HRID 44125
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HRID 44125 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 67.1%

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 6228Dimethylformamide용매2회

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 charged into a 2 L three-necked flask equipped with a thermometer, a cooling pipe, and a stirrer, followed by stirring at room temperature for 30 minutes. Then, 300 mL of a dimethylformamide solution containing 100 g (412 mmol) of 2-methyl-2-adamantyl chloroacetate was gradually added thereto. The resultant was heated to 40° C., and was then stirred for 4 hours. Following completion of the reaction, 2,000 mL of diethyl ether was added to the reaction mixture, followed by filtration of the resulting mixture. The obtained solution was washed three times with 500 mL of distilled water, followed by crystallization using a mixed solution containing 300 mL of toluene and 200 mL of heptane, thereby obtaining 78 g of an objective compound in the form of a colorless solid (yield: 67%, GC purity: 99%).

후처리

  1. customequipped with a thermometer
  2. additionwas gradually added
  3. temperatureThe resultant was heated to 40° C.
  4. stirringwas then stirred for 4 hours
  5. additionwas added to the reaction mixture
  6. filtrationfollowed by filtration of the resulting mixture
  7. washThe obtained solution was washed three times with 500 mL of distilled water
  8. customfollowed by crystallization
  9. additioncontaining 300 mL of toluene and 200 mL of heptane

출처 및 근거

ORD 기록
ord-cb6f037f6e0d4508a7afb2f2cd48f6fc
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541157B2

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