Diethyl Ether → HCID 54099087, compound

HRID 2057650Notes

Reaction equation

HRID 2057650 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29].[OH-].[Na+]>O>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54569210HCID 54569210, compound

Product 1

HCID 54099087HCID 54099087, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred slurry of 18.1 g. lithium aluminum hydride in 460 ml. ether is added dropwise a solution of 61.3 g. 12-(2-thienyl)-11-dodecenoic acid in 140 ml. ether at a rate such that gentle reflux is maintained. After four additional hours at reflux, the solution is cooled in ice and treated sequentially with 18.1 ml. water, 18.1 ml. 15% sodium hydroxide, solution and 54.3 ml. water. The precipitate is filtered and washed several times with ether. The combined ether fractions are washed with brine, dried, and evaporated. Distillation of the residual yields 12-(2-thienyl)-11-dodecenol as a semicrystalline mass.

Workup

  1. temperatureis maintained
  2. temperatureAfter four additional hours at reflux
  3. temperaturethe solution is cooled in ice
  4. additiontreated sequentially with 18.1 ml
  5. filtrationThe precipitate is filtered
  6. washwashed several times with ether
  7. washThe combined ether fractions are washed with brine
  8. customdried
  9. customevaporated
  10. distillationDistillation of the

Sources & evidence

ORD record
ord-e1f4b4229c3a42249d7783774adaecab
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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