Water → 2,2-Bis(4-nitrobenzyl)-1,3-propandiol

HRID 511715Notes

Reaction equation

HRID 511715 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)([C:13](O)=[O:14])[C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].O>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)([CH2:10][OH:11])[CH2:13][OH:14])=[CH:26][CH:27]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 229285922,2-Bis(4-nitrobenzyl)malonic acid

Product 1

HCID 229286162,2-Bis(4-nitrobenzyl)-1,3-propandiol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.00 g (10.69 mmol) 2,2-bis(4-nitrobenzyl)malonic acid is dissolved in 40 ml tetrahydrofuran and added dropwise in a the course of 2 hours to 64.1 ml (64.1 mmol) of a borane-tetrahydrofuran complex 1.0 M solution in tetrahydrofuran. After 19 hours at 25° C., 50 ml water is carefully added. 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, 3.77 g (97%) of 2,2-bis(4-nitrobenzyl)-1,3-propandiol 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, 3.77 g (97%) of 2,2-bis(4-nitrobenzyl)-1,3-propandiol as white powder is used without further purification

Sources & evidence

ORD record
ord-b97dd28a6a714901bd41e8f7d65fb0bd
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Reaction notes

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