Formic Acid → 2,5-Dimethylhexane-2,5-diyl bis(2-(formyloxy)acetate)

HRID 1802998Notes

Reaction equation

HRID 1802998 reaction equation
[CH:1]([OH:3])=[O:2].C(N(CC)CC)C.Cl[CH2:12][C:13]([O:15][C:16]([CH3:28])([CH2:18][CH2:19][C:20]([O:23][C:24](=[O:27])[CH2:25]Cl)([CH3:22])[CH3:21])[CH3:17])=[O:14].[C:29]([O:32]CC)(=[O:31])C>>[CH:1]([O:3][CH2:12][C:13]([O:15][C:16]([CH3:28])([CH2:18][CH2:19][C:20]([O:23][C:24](=[O:27])[CH2:25][O:32][CH:29]=[O:31])([CH3:22])[CH3:21])[CH3:17])=[O:14])=[O:2]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 582821502,5-Dimethylhexane-2,5-diyl bis(2-chloroacetate)

Product 1

HCID 582821452,5-Dimethylhexane-2,5-diyl bis(2-(formyloxy)acetate)

Procedure

Formic acid (67) (0.921 g, 20 mmol) and triethylamine (2.226 g, 22 mmol) were combined and stirred for 30 minutes. Compound (61) (0.299 g, 1 mmol) was then added and stirred for three days. The solution was dissolved in 10 mL of ethyl acetate and the precipitate was filtered and washed with 10 mL diethylether. The combined filtrate was then washed with brine and dried with sodium sulfate. The solvent was evaporated to get dark brown viscous oil. 1H NMR (400 MHz, CDCl3): δ 1.44 (s, 12H), 1.80 (s, 4H), 4.57 (s, 4H), 8.11 (s, 2H).

Workup

  1. stirringstirred for three days
  2. filtrationthe precipitate was filtered
  3. washwashed with 10 mL diethylether
  4. washThe combined filtrate was then washed with brine
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was evaporated
  7. customto get dark brown viscous oil

Sources & evidence

ORD record
ord-9e4ff99cccd147fa8a166c785472c694
Source dataset
uspto-grants-2013_01
Patent number
US08349990B2

Reaction notes

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