Glyoxylic Acid → 4-nitroheptanedial

HRID 1918274Notes

Reaction equation

HRID 1918274 reaction equation
[OH:1][CH:2](S([O-])(=O)=O)[CH2:3][CH2:4][CH:5]([N+:14]([O-:16])=[O:15])[CH2:6][CH2:7][CH:8]([OH:13])S([O-])(=O)=O.[Na+].[Na+].C(O)(=O)C=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[N+:14]([CH:5]([CH2:4][CH2:3][CH:2]=[O:1])[CH2:6][CH2:7][CH:8]=[O:13])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 516892Sodium BicarbonateHCID 71464326Disodium 1,7-dihydroxy-4-nitroheptane-1,7-disulfonate

Product 1

HCID 109429314-nitroheptanedial

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of sodium 1,7-dihydroxy-4-nitro-heptane-1,7-disulfonate, 9, (219 g, 0.57 mol) in methylene chloride (1.6 L) was added a solution of glyoxylic acid (160 g, 1.7 mol) and sodium bicarbonate (150 g, 1.78 mol) in water (2 L). The resulting mixture was stirred at room temperature for 30 to 60 minutes until all solids were dissolved. The organic layer was split and the aqueous layer was extracted with methylene chloride twice (2×400 ml). Combined extracts were then concentrated to give a colorless oil. The product was carried to next step without further purification. Yield: 85 g, 86%. 1H NMR (400 MHz, CDCl3) δ 2.09-2.24 (m, 4H), 2.58 (m, 4H), 4.61 (m, 1H), 9.77 (s, 2H). 13C NMR δ 26.2, 39.9, 86.9, 200.0.

Workup

  1. dissolutionwere dissolved
  2. customThe organic layer was split
  3. extractionthe aqueous layer was extracted with methylene chloride twice (2×400 ml)
  4. concentrationCombined extracts were then concentrated
  5. customto give a colorless oil
  6. customThe product was carried to next step without further purification

Sources & evidence

ORD record
ord-bfc645af5efc441dbe0b4ae22c73734c
Source dataset
uspto-grants-2013_12
Patent number
US08618314B2

Reaction notes

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