Toluene → 1,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

HRID 52387

反応式

HRID 52387 の反応式
[OH-].[Na+].C1(C)C=CC=CC=1.[OH:10][CH:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([CH3:19])[C:13]([CH3:21])([CH3:20])[CH2:12]1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:19][N:14]1[C:13]([CH3:21])([CH3:20])[CH2:12][CH:11]([O:10][CH2:22][CH:24]2[O:26][CH2:25]2)[CH2:16][C:15]1([CH3:17])[CH3:18]

参加物

7

反応物 4

HCID 1140TolueneHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-

生成物 1

HCID 142745051,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

実験手順

300 g (7.5 mol) of sodium hydroxide are dissolved in 300 g of water under an argon atmosphere in a 2.5 l sulfonation flask fitted with mechanical stirrer, condenser and 500 l dropping funnel. 750 ml of toluene, 48.4 g (0.15 mol) of tetrabutylammonium bromide and 257 g (1.5 mol) of 4-hydroxy-1,2,2,6,6-pentamethylpiperidine are added. 347 g of epichlorohydrin (3.75 mol) are added dropwise at 60° C. over the course of 1.5 hours, and the mixture is subsequently stirred at the same temperature for a further 4 hours. The reaction solution is poured in 3 l of ice water, and the organic phase is separated off, dried using sodium sulfate and evaporated. The residue is distilled at 0.05 mmHg over a Vigreux column, and the fraction of boiling point 71°-72° C. is collected. Yield: 205 g (60%). GC: >99%.

後処理

  1. customfitted with mechanical stirrer, condenser
  2. customthe organic phase is separated off
  3. customdried
  4. customevaporated
  5. distillationThe residue is distilled at 0.05 mmHg over a Vigreux column
  6. customthe fraction of boiling point 71°-72° C. is collected

出典と根拠

ORDレコード
ord-313ddd5281a040698a4b9baad84c5756
出典データセット
uspto-grants-1997_04
特許番号
US05616637

関連ノート

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