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

HRID 974210
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HRID 974210 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 66133Benzyl triethylammonium chloride촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11b7ead8b8d24e0d8968afbee00b18a3
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05068300

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