Hexadecanolide → 1,16-Hexadecanediol

HRID 526288

반응식

HRID 526288 반응식
[C:1]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:16]([OH:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:18]

참가 물질

5

반응물 3

HCID 7984HexadecanolideHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 821841,16-Hexadecanediol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Under an argon atmosphere, 16-Hexadecanolide (4.860 g, 18.5 mmol) in THF (80 mL) was added with stirring to a suspension of lithium aluminium hydride (1.280 g, 33.7 mmol, 1.8 eq.) in THF (160 mL) at 0° C. Stirring was continued at this temperature for 1 h and for 3 more hours at r.t. Potassium sodium tartrate solution was carefully dropped to this mixture with stirring. The phases were separated and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic layer was dried over MgSO4. After evaporation of the solvent, the product was isolated as a white solid, which was used for the next step without purification. Yield: 4.598 g (96%).

후처리

  1. stirringwith stirring
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether (3×100 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. customAfter evaporation of the solvent
  6. customthe product was isolated as a white solid, which
  7. customwas used for the next step without purification

출처 및 근거

ORD 기록
ord-39f3531984b74b968c3fe16ee105c255
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345791B2

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