Sulfuric Acid → 4''-n-Pentoxy-[1,1':4',1'']-terphenyl-carboxylic acid

HRID 1884212

반응식

HRID 1884212 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](O)=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:22][C:23]1[CH:28]=[CH:27]C(B(O)O)=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[C:32](=O)([O-:34])[O-:33].[Na+].[Na+].S(=O)(=O)(O)O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CO.C(O)CO>[CH2:17]([O:22][C:23]1[CH:28]=[CH:27][C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[C:6]([C:32]([OH:34])=[O:33])=[CH:7][CH:2]=[CH:3][CH:4]=3)=[CH:13][CH:12]=2)=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 8167304'-Iodobiphenyl-4-carboxylic acidHCID 46848884-Pentyloxyphenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 235087594''-n-Pentoxy-[1,1':4',1'']-terphenyl-carboxylic acid

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 445171Poly(ethylene glycol) dimethyl ether (NHD)용매

반응 조건

온도
95 °C

실험 절차

32.4 g of 4′-iodobiphenyl-4-carboxylic acid are introduced together with 25.8 g of glycol ester of 4-n-pentoxyphenylboronic acid and 15.9 g of sodium carbonate into 300 ml of methanol/ethylene glycol 9:1 and, while stirring vigorously, 70 mg of PdCl2(PPh3)2 are added, and the mixture is stirred under reflux for 6 hours. The hot reaction mixture is cautiously poured into a mixture of 30 g of 37% strength sulfuric acid and 200 g of water, and the mixture is heated at 90-100° C. for 30 minutes. After filtration and washing with water, the crude product is dried at 80° C./100 bar and then recrystallized from dimethylacetamide. This affords after drying 28.9 g (80%) of 4″-n-pentoxy-[1,1′:4′,1″]-terphenyl-4-carboxylic acid with a purity of >99%.

후처리

  1. stirringthe mixture is stirred
  2. temperatureunder reflux for 6 hours
  3. filtrationAfter filtration
  4. washwashing with water
  5. dry with materialthe crude product is dried at 80° C./100 bar
  6. customrecrystallized from dimethylacetamide
  7. customThis affords
  8. dry with materialafter drying 28.9 g (80%) of 4″-n-pentoxy-[1,1′:4′,1″]-terphenyl-4-carboxylic acid with a purity of >99%

출처 및 근거

ORD 기록
ord-e00d326f7d3248f486dd4b004ac98506
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762315B1

연결된 노트

불러오는 중…