Benzyl Chloride → HCID 15630621, compound

HRID 1415343Notes

Reaction equation

HRID 1415343 reaction equation
[OH:1][CH2:2][C:3]1([CH3:10])[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1.[H-].[Na+].[H][H].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:1][CH2:2][C:3]1([CH3:10])[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 11105499(2,2,4-Trimethyl-1,3-dioxolan-4-yl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 15630621HCID 15630621, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane (10g, prepared as in (b)) was added dropwise to a stirred suspension of sodium hydride (3g, 50% dispersion in oil) in dry toluene (150 ml). When the addition was complete the solution was heated under reflux until no more hydrogen was evolved. Benzyl chloride (7.85g) was added to the refluxing solution over a period of 15 minutes, after which the solution was heated under reflux for a further 3 hours. The solution was then cooled, washed with water (3 × 30 ml), dried and the solvent removed under reduced pressure. The residual oil was fractionally distilled to give the desired product as a colorless liquid having a b.p. 80° C at 0.2 mm Hg.

Workup

  1. additionWhen the addition
  2. temperaturewas heated
  3. temperatureafter which the solution was heated
  4. temperatureunder reflux for a further 3 hours
  5. temperatureThe solution was then cooled
  6. washwashed with water (3 × 30 ml)
  7. customdried
  8. customthe solvent removed under reduced pressure
  9. distillationThe residual oil was fractionally distilled

Sources & evidence

ORD record
ord-5535d63cf32446bf9b990b74050c63bd
Source dataset
uspto-grants-1977_01
Patent number
US04004911

Reaction notes

Loading…