Hydrochloric Acid → 3,4,5-Tris(octadecyloxy)cyclohexylmethyl alcohol

HRID 537612ノート

反応式

HRID 537612 の反応式
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([C:64](OC)=[O:65])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CC(C[AlH]CC(C)C)C.Cl>C1COCC1>[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][OH:65])[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 86654892Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate

生成物 1

HCID 866457853,4,5-Tris(octadecyloxy)cyclohexylmethyl alcohol収率 100.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate (70.0 g, 73.9 mmol) was dissolved in THF (1050 ml), and DIBAL (1.0 mol/L toluene solution, 200 ml, 200 mmol) was added dropwise at 0° C. over 40 min under a nitrogen atmosphere. After stirring at room temperature for 2 hr, 0.2N hydrochloric acid (50 ml) was added dropwise at 0° C. to quench the reaction. The solvent was evaporated to about half, and the residue was dissolved in chloroform (700 ml). The mixture was washed three times with 1N hydrochloric acid (300 ml), once with 5% aqueous sodium hydrogen carbonate solution (300 ml), and once with 20% brine (300 ml). The solvent was evaporated, and the residue was precipitated with methanol (700 ml), and washed with acetonitrile to give 3,4,5-tris(octadecyloxy)cyclohexylmethyl alcohol (68.2 g, 74.2 mmol, 100%).

後処理

  1. customto quench
  2. customthe reaction
  3. customThe solvent was evaporated to about half
  4. dissolutionthe residue was dissolved in chloroform (700 ml)
  5. washThe mixture was washed three times with 1N hydrochloric acid (300 ml)
  6. customThe solvent was evaporated
  7. customthe residue was precipitated with methanol (700 ml)
  8. washwashed with acetonitrile

出典と根拠

ORDレコード
ord-9bc0c834651f4bfd993b6de31d7c4c14
出典データセット
uspto-grants-2014_10
特許番号
US08859732B2

反応ノート

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