Formaldehyde → 11-Dodecen-1-ol

HRID 964542Notes

Reaction equation

HRID 964542 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 synthetic protocol for inventive compound no. 2525 (see above for chemical name and formula). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (Syn. Comm. 1984, 14, 591-597: 12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 minutes and the reaction was 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) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg, yielding a clear liquid alcohol, 11-dodecen-1-ol (6.53 g, 67 %, b.p. 105°-107° C.).

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hours
  3. extractionextracted with diethyl ether (2×100 ml)
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. customevaporated
  6. customto give a residue which
  7. distillationwas distilled at 2 mm Hg

Sources & evidence

ORD record
ord-16665324c9744e6e811e32e21d9c6a77
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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