Hydrochloric Acid → Benzene, [(4-pentynyloxy)methyl]-

HRID 2223333Notes

Reaction equation

HRID 2223333 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].[H-].[Na+].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CN(C=O)C>[CH2:9]([O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 793464-Pentyn-1-ol

Product 1

HCID 563055Benzene, [(4-pentynyloxy)methyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

15 ml of 4-pentin-1-ol is added in drops at 0° C. to a suspension of 17.4 g of sodium hydride (55%) in 200 ml of DMF, and it is stirred for 1 hour at 0° C. Then, 30 ml of benzyl bromide is added in drops at this temperature, and it is stirred for another 2 hours at 0° C. Then, the reaction is carefully neutralized with 1N hydrochloric acid. The phase separation is carried out between diethyl ether and water, and the aqueous phase is extracted several times with diethyl ether. The combined organic phases are washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. The residue is distilled in an oil pump vacuum, and 22.7 g of 5-benzyloxypent-1-ine is obtained as a colorless oil.

Workup

  1. stirringis stirred for another 2 hours at 0° C
  2. customThe phase separation
  3. extractionthe aqueous phase is extracted several times with diethyl ether
  4. washThe combined organic phases are washed with water, saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. distillationThe residue is distilled in an oil pump vacuum

Sources & evidence

ORD record
ord-45431796474b45658643f599789ea793
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

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