Hydrochloric Acid → hydroxymethyl-4,4'-Dinitro 1,1'-biphenyl

HRID 2193517Notes

Reaction equation

HRID 2193517 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:22](O)=[O:23])[C:7]([C:10]2[C:11](C(O)=O)=[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>[OH:23][CH2:22][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

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

Product 1

HCID 86625101hydroxymethyl-4,4'-Dinitro 1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.6 g (10.83 mmol) 4,4′-Dinitro-1,1′-biphenyl-2,2′-dicarboxylic acid are dissolved in 25 ml tetrahydrofuran and added dropwise 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 are 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 2,2′-bis(hydroxymethyl-4,4′-Dinitro 1,1′-biphenyl 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 2,2′-bis(hydroxymethyl-4,4′-Dinitro 1,1′-biphenyl as white powder is used without further purification

Sources & evidence

ORD record
ord-adcb2c650a7b4926a5bd826ccae87fee
Source dataset
uspto-grants-2012_12
Patent number
US08329823B2

Reaction notes

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