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

HRID 909975
ノート
印刷プレビュー

反応式

HRID 909975 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

HCID 581059672-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol収率 67.1%

試薬・触媒・溶媒 3

HCID 180Acetone
溶媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-80a4b0ea87fa4904bb3574ed22b5f4e2
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08021823B2

反応ノート

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