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Toluene → 4,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

HRID 974210
ノート
印刷プレビュー

反応式

HRID 974210 の反応式
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]([OH:20])([C:18]#C)[CH3:17].C1(P([C:34]2[CH:39]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-:40].[Na+].[C:42]1([CH3:48])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Cu]I>[C:16]([O:20][C:48]([C:42]1[CH:47]=[CH:46][C:45]([C:39]#[C:34][C:10]2[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14])=[CH:8][CH:9]=2)=[CH:44][CH:43]=1)=[O:40])([CH3:18])([CH3:17])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 1140TolueneHCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 11334366Tert-butyl 4-bromobenzoate

生成物 1

HCID 148475264,4'-Tolan-dicarboxylic acid di-tert.-butyl ester

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 66133Benzyl triethylammonium chloride触媒

実験手順

A mixture of 514 g of 4-bromobenzoic acid tert.-butyl ester, 88.25 g of 2-methyl-3-butyn-2-ol and 74.5 g of triphenylphosphine in 1250 ml of toluene is added to 7.1 g of benzyl triethylammonium chloride, 9.55 g of copper(I)iodide and 14 g of (Pφ3)2PdCl2 and the reaction mixture is stirred at reflux for 48 hours after the addition of 750 ml of 5.5 N NaOH. The organic phase is separated off, dried and concentrated by evaporation. 430 g of moist crude product are stirred up in 550 ml of methanol and suction filtered. 248 g of 4,4'-tolan-dicarboxylic acid di-tert.-butyl ester are obtained and may be further purified by recrystallisation from acetonitrile.

後処理

  1. temperatureat reflux for 48 hours
  2. customThe organic phase is separated off
  3. customdried
  4. concentrationconcentrated by evaporation
  5. stirring430 g of moist crude product are stirred up in 550 ml of methanol
  6. filtrationsuction filtered

出典と根拠

ORDレコード
ord-11b7ead8b8d24e0d8968afbee00b18a3
出典データセット
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05068300

反応ノート

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