Water → ((Prop-2-yn-1-yloxy)methyl)benzene

HRID 1780050Notes

Reaction equation

HRID 1780050 reaction equation
O.[OH-].[Na+].[CH2:4]([OH:7])[C:5]#[CH:6].[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH2:4]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]#[CH:6]

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl Chloride2×HCID 7859Propargyl alcoholHCID 14798Sodium Hydroxide

Product 1

HCID 6917484((Prop-2-yn-1-yloxy)methyl)benzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

In preparing the alkynyl intermediate (used as a second reaction product), water (800 ml) was added to sodium hydroxide pellets (800 g) over 20 minutes using a cooling ice bath. The solution was further cooled to 10° C. Hexane (800 ml) and tetrabutylammonium bromide were added followed by propargyl alcohol (237 ml), dropwise over 20 minutes with ice bath cooling. The reaction was allowed to warm to 30° C. during the addition and benzyl chloride (414 ml) was added over 20 minutes, avoiding exothermic conditions. The reaction was warmed to 40° C. for 6 hours at which time gas chromotagraphy analysis indicated all the benzyl chloride had been consumed. After cooling to 25° C., water (800 ml) was added over 10 minutes with ice bath cooling. During this period, the temperature rose to 30° C. The lower, clear aqueous phase was removed and 25% saturated sodium chloride (800 ml) was added to the turbid upper phase. The two phases became clear and the layers were separated. The isolated organic phase was dried with sodium sulphate (20 g) and the hexane evaporated to afford benzyl propargyl ether as an orange oil (515 g, 98.5% pure). The other 1.5% is benzyl ether produced from benzyl alcohol formed in the reaction.

Workup

  1. temperaturecooling
  2. additionwas added over 20 minutes
  3. temperatureThe reaction was warmed to 40° C. for 6 hours at which time gas chromotagraphy analysis
  4. customhad been consumed
  5. temperatureAfter cooling to 25° C.
  6. additionwater (800 ml) was added over 10 minutes with ice bath
  7. temperaturecooling
  8. waitDuring this period
  9. customrose to 30° C
  10. customThe lower, clear aqueous phase was removed
  11. addition25% saturated sodium chloride (800 ml) was added to the turbid upper phase
  12. customthe layers were separated
  13. dry with materialThe isolated organic phase was dried with sodium sulphate (20 g)
  14. customthe hexane evaporated

Sources & evidence

ORD record
ord-21c9fb5944e14b3bb94ddb47eb1b4ed6
Source dataset
uspto-grants-1997_05
Patent number
US05629423

Reaction notes

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