Triethylamine → 4-n-Undecanoyloxy-4'-hydroxy-biphenyl

HRID 442592ノート

反応式

HRID 442592 の反応式
[CH3:1][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:3].C(N(CC)CC)C.[C:25](Cl)(=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:3])[CH2:1][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 87287Undecanoyl chlorideHCID 144384094-Methylcarbonyloxy-4'-hydroxybiphenyl

生成物 1

HCID 539939534-n-Undecanoyloxy-4'-hydroxy-biphenyl収率 39.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4-methylcarbonyloxy-4'-hydroxybiphenyl (2.3 g) and triethylamine (1.1 g) in methylene chloride (50 ml) was gradually added dropwise undecanoyl chloride (n-C10H21COCl) (2.1 g). Dimethylaminopyridine (0.3 g) was further added thereto and the mixture was stirred for 24 hours. After the solvent was distilled off, the residue was added to tetrahydrofuran containing tert-butylamine and the mixture was refluxed at 70° C. for 2 hours and hydrolyzed. After the solvent was distilled off, dilute hydrochloric acid was added to the residue to render the solution neutral and the solution was extracted with diethyl ether. After the solvent was distilled off, the residue was washed with hexane and recrystallized from water/ethanol (1/9) solution to obtain the titled compound (about 1.4 g).

後処理

  1. distillationAfter the solvent was distilled off
  2. additionthe residue was added to tetrahydrofuran
  3. additioncontaining tert-butylamine
  4. distillationAfter the solvent was distilled off
  5. additiondilute hydrochloric acid was added to the residue
  6. extractionthe solution was extracted with diethyl ether
  7. distillationAfter the solvent was distilled off
  8. washthe residue was washed with hexane
  9. customrecrystallized from water/ethanol (1/9) solution

出典と根拠

ORDレコード
ord-67403f27f5e745d7a42c1dd6a376f3cb
出典データセット
uspto-grants-1999_04
特許番号
US05891359

反応ノート

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