Hexane → HCID 13851728, compound

HRID 1722244Notes

Reaction equation

HRID 1722244 reaction equation
C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1(C#C)C=CC=CC=1.[C:20]([O:28][CH2:29][CH2:30][O:31]CCl)(=O)[C:21]1C=CC=C[CH:22]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[C:8]1([C:22]#[C:21][CH2:20][O:28][CH2:29][CH2:30][OH:31])[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=1

Participants

9

Reactant 5

HCID 8058HexaneHCID 10821PhenylacetyleneHCID 14798Sodium HydroxideHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 178418339Butyllithium

Product 1

HCID 13851728HCID 13851728, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

Butyl lithium in hexane (30 mmol) was added to phenylacetylene (3.29 ml, 30 mmol) in dry THF (20 ml) at -78° C. The mixture was allowed to reach room temperature, cooled to 78° C. and 2-chloromethoxyethyl benzoate (6.4 g 30 mmol) added. The mixture was kept at 0° C. for 24 hours, quenched with water and extracted into ether. The crude product obtained from the organic phase was treated with 8% sodium hydroxide in ethanol (100 ml) and heated under reflux for 0.5 hours. The crude product was poured into water and extracted into ether. The ether extracts were washed with water, dried and the solvent removed to give 5 g of 2-(3-phenyl-2-propynoxy)ethanol.

Workup

  1. customto reach room temperature
  2. customquenched with water
  3. extractionextracted into ether
  4. customThe crude product obtained from the organic phase
  5. temperatureheated
  6. temperatureunder reflux for 0.5 hours
  7. extractionextracted into ether
  8. washThe ether extracts were washed with water
  9. customdried
  10. customthe solvent removed

Sources & evidence

ORD record
ord-b34d16dda37443159cb233e834d34791
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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