Acetic Anhydride → Diethyl ((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methyl)phosphonate

HRID 1681445

반응식

HRID 1681445 반응식
[OH:1][C:2]1[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][C:5]([CH2:6]N(C)C)=[CH:4][C:3]=1[C:16]([CH3:19])([CH3:18])[CH3:17].[P:20]([O:27]CC)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23].C(OC(=O)C)(=O)C>>[OH:1][C:2]1[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][C:5]([CH2:6][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])=[CH:4][C:3]=1[C:16]([CH3:19])([CH3:18])[CH3:17]

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 31215Triethyl phosphiteHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-

생성물 1

HCID 70421Diethyl ((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methyl)phosphonate수율 92.6%

반응 조건

온도
60 °C

실험 절차

A thermostatically controllable reactor is charged with 553.8 g (2.1 mol) of (4-hydroxy-3,5-di-tert-butylbenzyl)dimethylamine und 450 g of petroleum ether 100/140. With stirring and blanketing with inert gas, the reaction mixture is heated to 60° C. and 366.4 g (2.2 mol) of triethyl phosphite are run into the clear solution. With cooling, 225.1 g (2.2 mol) of acetic anhydride are then added dropwise over 2 hours at 60° C., and stirring is continued for 1 hour at 60° C. The solvent is removed by distillation until the temperature is 115° C. The residual reaction solution is washed with 4×250 ml of water at 75° C. and dried by azeotropic distillation. Upon cooling to room temperature, the product crystallises and is filtered with suction, washed with petroleum ether 100/140 and dried, giving 693.2 g (92.6% of theory) of colourless diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate of m.p. 119°-121° C.

후처리

  1. temperatureWith cooling
  2. stirringstirring
  3. customThe solvent is removed by distillation until the temperature
  4. customis 115° C
  5. washThe residual reaction solution is washed with 4×250 ml of water at 75° C.
  6. customdried by azeotropic distillation
  7. temperatureUpon cooling to room temperature
  8. customthe product crystallises
  9. filtrationis filtered with suction
  10. washwashed with petroleum ether 100/140
  11. customdried

출처 및 근거

ORD 기록
ord-3b519c1213ce4843b4d0f146172256cd
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05171873

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