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

HRID 2090151Notes

Reaction equation

HRID 2090151 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 tetrahydro-furan. 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-c745628ea82349db8fc225def2e0b54a
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

Loading…