Benzyl Chloride → Benzyl 2-benzyloxymethyl-4,4-dimethoxybutyl ether

HRID 2291845Notes

Reaction equation

HRID 2291845 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:12][CH3:13])[CH2:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9].[H][H].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.C1COCC1.C(O)C>[CH2:16]([O:9][CH2:8][CH:7]([CH2:6][CH:5]([O:4][CH3:3])[O:12][CH3:13])[CH2:10][O:11][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 117895481,3-Propanediol, 2-(2,2-dimethoxyethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 14843250Benzyl 2-benzyloxymethyl-4,4-dimethoxybutyl etherYield 121.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (55% in oil, 32.72 g, 0.75 mol) was washed twice with n-hexane and suspended in 200 ml of THF. 4,4-Dimethoxy-2-(hydroxymethyl)butanol (49.26 g, 0.3 mol) was added dropwise to maintain a gentle evolution of hydrogen gas. Then benzyl chloride (94.94 g, 0.45 mol) was added during 30 min. and the mixture was refluxed over-night, cooled, diluted with 50 ml of ethanol, and evaporated in vacuum. The residue was suspended in about 200 ml of water and extracted with 3×100 ml of ether. The combined organic extracts were dried (MgSO4) and distilled in vacuum. The title compound (94.34 g, 91%) was obtained at 197°-200° C. (0.01 mm Hg).

Workup

  1. temperaturethe mixture was refluxed over-night
  2. temperaturecooled
  3. customevaporated in vacuum
  4. extractionextracted with 3×100 ml of ether
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-25070d07298347f98cf2880cac285b1a
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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