Formaldehyde → 11-Dodecen-1-ol

HRID 441134Notes

Reaction equation

HRID 441134 reaction equation
[CH2:1](N1C(=O)C2N(C)C=NC=2N(C)C1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[Mg].II.C(Br)CCCCCCCCC=C.C=[O:42].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([OH:42])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 807IodineHCID 25517Ammonium ChlorideHCID 28414811-Bromo-1-undeceneHCID 5462224MagnesiumHCID 232958711-(11-Dodecenyl)-3,7-dimethylxanthine

Product 1

HCID 52072511-Dodecen-1-olYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates the synthesis of 1-(11-Dodecenyl)-3,7-dimethylxanthine (CT2516). 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) in tetrahydrofuran (30 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hr. 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 to afford 11-dodecenyl alcohol as a clear liquid (6.53 g, 67%, b.p. 105°-107° C.).

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hr
  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-5dcd52dba72f4bf09da0d12699644345
Source dataset
uspto-grants-1996_05
Patent number
US05521315

Reaction notes

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