(+-)-alpha-Pinene → Tetraethyl-para-menthane-2,6-diyldiphosphonate

HRID 2052227

반응식

HRID 2052227 반응식
[P:1]([OH:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].C(O[O:14][C:15]([CH3:18])(C)C)(C)(C)C.[CH3:19][C:20]1[CH:25]2[C:26]([CH3:28])([CH3:27])[CH:23]([CH2:24]2)[CH2:22][CH:21]=1>>[CH2:3]([O:2][P:1]([CH:21]1[CH2:22][CH:23]([CH:26]([CH3:27])[CH3:28])[CH2:24][CH:25]([P:1](=[O:5])([O:14][CH2:15][CH3:18])[O:2][CH2:3][CH3:4])[CH:20]1[CH3:19])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:4]

참가 물질

4

반응물 3

HCID 6654(+-)-alpha-PineneHCID 8033Di-tert-butyl peroxideHCID 12977Ethyl phosphite, (C2H5O)2(OH)P2회

생성물 1

HCID 131711680Tetraethyl-para-menthane-2,6-diyldiphosphonate수율 70%

실험 절차

To a 5-liter vessel equipped with a mechanical stirrer was added 863 ml (6.7 mol) of diethyl hydrogen phosphite (DEHP). The stirred DEHP was heated to 140° and then 12.3 ml (0.067 mol) of di-tertiary-butyl peroxide was added. Finally, α-pinene, 211 ml (1.3 mol), was added dropwise over a period of 10-30 minutes while the reaction temperture was maintained at 140°-150°. This mixture was heated for 5 hours at 140°, cooled at room temperature, and then distilled in vacuo to yield 54.2 g (0.2 mol; 15.4%) of diethyl para-menth-6-en-2-ylphosphonate, bp=180°-185° (1.2 mm), and 376.5 g (0.91 mol, 70.0%) of tetraethyl-para-menthane-2,6-diyldiphosphonate), bp=198° (0.4 mm). The NMR spectrum showed an A2B3 pattern corresponding to the ethyl groups at 4.12δ and 1.35δ along with the remainder of the proton signals between 2.5δ and 0.8δ.

후처리

  1. customTo a 5-liter vessel equipped with a mechanical stirrer
  2. temperaturewas maintained at 140°-150°
  3. temperatureThis mixture was heated for 5 hours at 140°
  4. distillationdistilled in vacuo

출처 및 근거

ORD 기록
ord-3ae75d1f74d24e68972b2a3d1e0d8f74
출처 데이터셋
uspto-grants-1980_01
특허 번호
US04183879

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