Formaldehyde → HCID 23124995, compound

HRID 916277Notes

Reaction equation

HRID 916277 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([CH:15]([CH2:20][CH2:21][CH2:22][CH3:23])[C:16]([O:18][CH3:19])=[O:17])[CH3:14].[CH2:24]=[O:25].[Cl-].[NH4+]>C1COCC1>[CH3:19][O:18][C:16](=[O:17])[C:15]([CH2:13][CH3:14])([CH2:24][OH:25])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 102491Methyl 2-ethylhexanoateHCID 178418339Butyllithium

Product 1

HCID 23124995HCID 23124995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5.2 ml (0.037 mol) of diisopropylamine are added dropwise at 0° C. to a solution of 12.9 ml (0.035 mol) of n-butyllithium (2.7 M in heptane) in 17 ml of THF, and the mixture is stirred at 0° C. for 15 min. Within approx. 10 min, 5 g (0.032 mol) of methyl 2-ethylhexanoate are added dropwise at 0° C., and the mixture is stirred at 0° C. for 30 min and subsequently admixed with 2.9 g (0.097 mol) of paraformaldehyde. After stirring at 0° C for 2 hours, a saturated aqueous solution of ammonium chloride (20 ml) is added and the mixture is stirred at RT for 2 h. The organic phase is removed, the aqueous phase is re-extracted once with 20 ml of MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 83% (GC).

Workup

  1. waitWithin approx. 10 min
  2. stirringthe mixture is stirred at 0° C. for 30 min
  3. stirringAfter stirring at 0° C for 2 hours
  4. stirringthe mixture is stirred at RT for 2 h
  5. customThe organic phase is removed
  6. extractionthe aqueous phase is re-extracted once with 20 ml of MTBE
  7. concentrationthe combined organic phases are concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8ec58d0698124dc49cf39a225e0d4686
Source dataset
uspto-grants-2007_09
Patent number
US07268253B2

Reaction notes

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