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

HRID 1671540Notes

Reaction equation

HRID 1671540 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 were 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 were carefully added. The reaction mixture was then partitioned between ethyl acetate and water; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue, 3.77 g (97%) of a white powder was used without further purification.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washthe organic phase was 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 a white powder was used without further purification

Sources & evidence

ORD record
ord-1f8de55cf92f459c8980b86d3816f6ec
Source dataset
uspto-grants-2011_08
Patent number
US07994273B2

Reaction notes

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