Hydrochloric Acid → HCID 19907982, compound

HRID 1534770Notes

Reaction equation

HRID 1534770 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[H-].[Na+].[OH:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.Cl>C1COCC1>[CH2:1]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[O:19])=[CH:20][CH:21]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromide2×HCID 24758Sodium hydrideHCID 11206592Benzaldehyde, 4-[2-(2-hydroxyethoxy)ethoxy]-

Product 1

HCID 19907982HCID 19907982, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

All three compounds were prepared by the etherification of the corresponding alcohols with allyl bromide. An example is presented below. Sodium hydride (3.06 g, 0.128 mol) was suspended in dried THF (150 mL). The solution was bubbled with nitrogen and cooled to 0° C. 4-[2-(2-Hydroxyethoxy)ethoxy]benzaldehyde (26.8 g, 0.128 mol) was added dropwise to the solution. After the addition was completed, the resulting solution was stirred for 0.5 hr. Allyl bromide (23.2 g, 0.191 mol) was added. The reaction mixture was stirred at room temperature for 3 hr, acidified with 5% HCl aqueous solution (100 ml) and extracted with ethyl acetate. The collected organic phase was washed with 2% sodium bicarbonate aqueous solution, water, saturated sodium chloride solution, and dried over anhydrous MgSO4. The solvent was evaporated in a rotavapor and the residual oil was vacuum distilled at 136° C./7 mmHg to yield 20 g (63%) of a colorless oily product 6. 1 H-NMR (CDCl3, TMS, δ in ppm): 3.56-4.27 (m, 10H, --CH2 --(O--CH2 --CH2)--2), 5.23 and 5.78 (m, 3H, CH2 =CH--), 7.05 and 7.77 (2d, 4 aromatic protons), 9.86 (s, 1H, --CHO).

Workup

  1. customThe solution was bubbled with nitrogen
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred at room temperature for 3 hr
  4. extractionextracted with ethyl acetate
  5. washThe collected organic phase was washed with 2% sodium bicarbonate aqueous solution, water, saturated sodium chloride solution
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent was evaporated in a rotavapor
  8. distillationdistilled at 136° C./7 mmHg

Sources & evidence

ORD record
ord-f76797e2990f4a47bb633c6dfbdba958
Source dataset
uspto-grants-1992_02
Patent number
US05091274

Reaction notes

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