Formaldehyde → 11-Dodecen-1-ol

HRID 1954143Notes

Reaction equation

HRID 1954143 reaction equation
[Mg].II.[CH2:4](Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14].[CH2:16]=[O:17].[Cl-].[NH4+]>O1CCCC1>[CH2:16]([OH:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH2:4]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 807IodineHCID 25517Ammonium ChlorideHCID 28414811-Bromo-1-undeceneHCID 5462224Magnesium

Product 1

HCID 52072511-Dodecen-1-olYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates a synthesis of 1-(11,12-Oxidododecyl)-3,7-dimethylxanthine (inventive compound no. 2518). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 mL) was added 10-undecenyl bromide (12.25 g, 53.0 mmol, available from MTM) in tetrahydrofuran (30 mL) over 30 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 5 minutes to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 mL) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (80 mL) is added and extracted with diethyl ether (2×100 mL). The combined organic extracts are dried using magnesium sulfate and evaporated to give a residue which is distilled at 2 mm Hg to yield 6.53 g (67% yield, b.p. 105-107° C.) of 11-dodecenyl alcohol as a clear liquid.

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hours
  3. extractionextracted with diethyl ether (2×100 mL)
  4. customThe combined organic extracts are dried
  5. customevaporated
  6. customto give a residue which
  7. distillationis distilled at 2 mm Hg

Sources & evidence

ORD record
ord-6c1214465f0e4a16b93733491c62669d
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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