Glyoxylic Acid → 4-nitroheptanedial

HRID 1669957Notes

Reaction equation

HRID 1669957 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-dbc4b317709444f29fe46d98f7819b21
Source dataset
uspto-grants-2011_08
Patent number
US07989653B2

Reaction notes

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