Benzene → HCID 54403115, compound

HRID 1606686Notes

Reaction equation

HRID 1606686 reaction equation
[C-]#[C-].[Li+].[Li+].[CH2:5](N)[CH2:6]N.[O:9]1CCCC1.[CH:14]1[CH:19]=CC=CC=1.[CH3:20][C:21](=O)[CH2:22][CH:23]=[CH:24][CH2:25][CH2:26][CH2:27]CC>O>[OH:9][C:5]([CH3:6])([CH2:20][CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:19]#[CH:14]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8028TetrahydrofuranHCID 73102388HCID 73102388, compoundHCID 178511344HCID 178511344, compound

Product 1

HCID 54403115HCID 54403115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 45.5 g. of lithium acetylide-ethylene diamine, 200 ml. of dry tetrahydrofuran, and 200 ml. benzene at 35°C. is stirred under nitrogen while 50 g. of 4-decen-2-one in 50 ml. of benzene is added slowly. The mixture is then stirred for about 2.5 hrs., and 130 ml. of water is added slowly. The mixture is heated under reflux for one hour, cooled, and extracted with ether. The ether extract is washed with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride, then is dried and evaporated under reduced pressure. The residue is distilled through a Vigreaux column giving a distillate comprising 3-hydroxy-3-methylundec-5-en-1-yne.

Workup

  1. additionA mixture of 45.5 g
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washis washed with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  8. customis dried
  9. customevaporated under reduced pressure
  10. distillationThe residue is distilled through a Vigreaux column

Sources & evidence

ORD record
ord-d1c5df1b707040f5871258c017b6081d
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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