Hydrochloric Acid → Tridec-12-en-1-ol

HRID 361543Notes

Reaction equation

HRID 361543 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]1[O:18][CH2:17]1.[Cl-].[NH4+].Cl>O1CCCC1>[CH2:16]([OH:18])[CH2:17][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH2:4]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 28414811-Bromo-1-undeceneHCID 5462224Magnesium

Product 1

HCID 15486836Tridec-12-en-1-olYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

This example illustrates a synthesis of 1-(12,13-Oxidotridecyl)-3,7-dimethylxanthine (inventive compound no. 2562). To a suspension of magnesium (4.12 g, 172 mmol) and a crystal of iodine in tetrahydrofuran (40 mL) was added 10-undecenyl bromide (8.00 g, 34.3 mmol) 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 solution of ethylene oxide (2.65 g, 60.0 mmol) in tetrahydrofuran (30 mL) and stirred at 25° C. for 16 hours. Saturated ammonium chloride (100 mL) and 1M hydrogen chloride (200 mL) were added and extracted with diethyl ether (2×200 mL). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 1.5 mm Hg to afford 12-tridecenyl alcohol as a clear liquid (4.11 g, 61%, b.p. 98°-101° C.).

Workup

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hours
  3. extractionextracted with diethyl ether (2×200 mL)
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. customevaporated
  6. customto give a residue which
  7. distillationwas distilled at 1.5 mm Hg

Sources & evidence

ORD record
ord-c3fb57f73b7d44c5991283fe07573175
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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