Formaldehyde → HCID 86706083, compound

HRID 2176243Notes

Reaction equation

HRID 2176243 reaction equation
[OH:1][CH2:2][C:3]([CH2:12][OH:13])([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14]=O>Cl>[C:9]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:12][O:13][CH2:14][O:1][CH2:2]1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 13157916HCID 13157916, compound

Product 1

HCID 86706083HCID 86706083, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 2,2-bis(hydroxymethyl)-3-oxobutanoate (75 g, 0.39 mol) and 40% formaldehyde (360 mL) in concentrated hydrochloric acid (360 mL) was heated at 50° C. for 17 h. The two-phase solution was cooled to room temperature and extracted with ethyl acetate (2×200 mL). The combined organic phases were washed with water, dried over magnesium sulfate, and evaporated to give a residue, which was purified by flash column chromatography eluting with a continuous gradient of petroleum ether/ethyl acetate 15:1 to 9:1 to afford the title compound (33 g, 14%, 2 steps) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.25 (m, 3H), 2.31 (s, 3H), 4.25-4.19 (m, 4H), 4.35 (d, J=12.0 Hz, 2H), 4.77 (d, J=6.0 Hz, 1H), 4.82 (d, J=6.0 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a residue, which
  6. customwas purified by flash column chromatography
  7. washeluting with a continuous gradient of petroleum ether/ethyl acetate 15:1 to 9:1

Sources & evidence

ORD record
ord-652ace6fc9764c81a0d0ca68132934e2
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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