Toluene → 4-{[(2,6-Dichlorophenyl)methoxy]methyl}-4-ethyl-2,2-dimethyl-1,3-dioxolane

HRID 441689Notes

Reaction equation

HRID 441689 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:14]=1[CH2:15]Cl.[C:22]1(C)C=CC=C[CH:23]=1>>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:14]=1[CH2:15][O:8][CH2:7][C:5]1([CH2:22][CH3:23])[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1

Participants

5

Reactant 4

HCID 1140Toluene3×HCID 7528SolketalHCID 24758Sodium hydrideHCID 748322,6-Dichlorobenzyl chloride

Product 1

HCID 1866824-{[(2,6-Dichlorophenyl)methoxy]methyl}-4-ethyl-2,2-dimethyl-1,3-dioxolane

Procedure

A solution of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (32.0g) in toluene (25 ml) was added slowly to a stirred suspension of sodium hydride (9.6g of 50% dispersion in oil) in toluene (25 ml). After the addition the mixture was heated under reflux for 2 hours. 2,6-Dichlorobenzyl chloride (39.1g) in toluene (100 ml) was then added dropwise and the mixture heated under reflux for a further 4 hours. The cooled mixture was washed with water (×3) and dried and the solvent was removed under reduced pressure. The residual oil was distilled in vacuo to give the desired product b.p. 156°-162° C. at 1.5 mm Hg.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. temperaturethe mixture heated
  5. temperatureunder reflux for a further 4 hours
  6. washThe cooled mixture was washed with water (×3)
  7. customdried
  8. customthe solvent was removed under reduced pressure
  9. distillationThe residual oil was distilled in vacuo

Sources & evidence

ORD record
ord-da122ebb6e264a23baf61477bc9dfb2b
Source dataset
uspto-grants-1977_08
Patent number
US04042369

Reaction notes

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