Benzyl Chloride → HCID 21553974, compound

HRID 267784Notes

Reaction equation

HRID 267784 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1([CH3:15])[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([OH:14])[C:7]=2[O:6]1.[H][H].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)P(N(C)C)(N(C)C)=O.C(O)(=O)C>[CH3:3][O:4][C:5]1([CH3:15])[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]=2[O:6]1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 215539492-Methoxy-2-methyl-2H-1,3-benzodioxol-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 21553974HCID 21553974, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

To a suspension of sodium hydride (2.4 g., 0.1 mole) in freshly distilled hexamethyl-phosphoramide (24 ml.) is added dropwise with stirring under dry nitrogen a solution of 2-methoxy-2-methyl-4-hydroxy-1,3-benzodioxole (18.2 g., 0.1 mole) in hexamethylphosphoramide (36 ml.) and stirring is continued at ambient temperature until hydrogen evolution essentially ceases. Benzyl chloride (12.65 g., 0.1 mole) is added and the mixture stirred at 75°-80° C. for 5 hours. The mixture then is poured onto ice and adjusted to ca. pH 6 with acetic acid. The product is extracted with ether, and the ethereal solution washed with 2% sodium carbonate solution (50 ml.) and then with saturated sodium chloride solution. After drying over magnesium sulphate and then calcium sulfate, the ethereal solution is evaporated to give 2-methoxy-2-methyl-4-benzyloxy-1,3-benzodioxole which can be crystallized from di-isopropyl ether.

Workup

  1. additionis added dropwise
  2. stirringthe mixture stirred at 75°-80° C. for 5 hours
  3. additionThe mixture then is poured onto ice
  4. extractionThe product is extracted with ether
  5. washthe ethereal solution washed with 2% sodium carbonate solution (50 ml.)
  6. dry with materialAfter drying over magnesium sulphate
  7. customcalcium sulfate, the ethereal solution is evaporated

Sources & evidence

ORD record
ord-359c1ddd52454c1794313452cf0512fa
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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