Hydrochloric Acid → HCID 15267964, compound

HRID 511713

Reaction equation

HRID 511713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:22](O)=[O:23])[C:7]([C:10]2[C:11]([C:19](O)=[O:20])=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].O.Cl>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:22][OH:23])[C:7]([C:10]2[C:11]([CH2:19][OH:20])=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 97509(1,1'-Biphenyl)-2,2'-dicarboxylic acid, 4,4'-dinitro-

Product 1

HCID 15267964HCID 15267964, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.6 g (10.83 mmol) 4,4′-Dinitro-1,1′-biphenyl-2,2′-dicarboxylic acid is dissolved in 25 ml tetrahydrofuran and added drop wise in a the course of 1 hours to 65 ml (65.02 mmol) of a borane-tetrahydrofuran complex 1.0 M solution in tetrahydrofuran. After 19 hours at 25° C., 50 ml water is carefully added. After 1 h the solution is acidified to pH=1-2 with 10 ml 1N HCl solution and allowed to stirred for 30 min. The reaction mixture is then partitioned between ethyl acetate and water; the organic phase is washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue, 4.2 g of 4,4′-Dinitro-1,1′-biphenyl-2,2′-dimethanol as white powder is used without further purification.

Workup

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. washthe organic phase is washed repeatedly with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue, 4.2 g of 4,4′-Dinitro-1,1′-biphenyl-2,2′-dimethanol as white powder is used without further purification

Sources & evidence

ORD record
ord-b3575316b53947208f22b732357d6751
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Linked notes

Loading…