Sulfuric Acid → 158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

HRID 1884210Notes

Reaction equation

HRID 1884210 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:17]([O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[Na+].[Na+].S(=O)(=O)(O)O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C(O)CO>[CH2:17]([O:22][C:23]1[CH:24]=[CH:25][C:26]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:27][CH:28]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 4

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

Product 1

HCID 9798987158938-08-0 4-N-Pentoxyterphenyl-carbonic acid

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

162 g of 4′-iodobiphenyl-4-carboxylic acid are introduced together with 129 g of glycol ester of 4-n-pentoxyphenylboronic acid and 79.5 g of sodium carbonate into 1.5 l of ethylene glycol and, while stirring vigorously, 17.5 ml of a Pd(dba)2 solution are added and the mixture is stirred at 80° C. for 6 hours. The hot reaction mixture is cautiously poured into a mixture of 150 g of 37% strength sulfuric acid and 1,000 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 mbar and then recrystallized from dimethylacetamide. This affords after drying 132 g (73%) of 4″-n-pentoxyterphenyl-4-carboxylic acid with a purity of >99%.

Workup

  1. stirringthe mixture is stirred at 80° C. for 6 hours
  2. filtrationAfter filtration
  3. washwashing with water
  4. dry with materialthe crude product is dried at 80° C./100 mbar
  5. customrecrystallized from dimethylacetamide
  6. customThis affords
  7. dry with materialafter drying 132 g (73%) of 4″-n-pentoxyterphenyl-4-carboxylic acid with a purity of >99%

Sources & evidence

ORD record
ord-ef422a8eb7bc48e5bf6b9506e63bebb0
Source dataset
uspto-grants-2004_07
Patent number
US06762315B1

Reaction notes

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