Water → HCID 23321221, compound

HRID 280717Notes

Reaction equation

HRID 280717 reaction equation
[H-].[Na+].[CH3:3][CH:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH2:5][CH3:6].S(O[CH2:20][C:21]1[O:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[O:23][CH:22]=1)(C)(=O)=O.O>CN(C=O)C>[CH3:3][CH:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:20][C:21]2[O:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[O:23][CH:22]=2)=[CH:12][CH:13]=1)[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 138820044-(1-Methyl-1-propyloxy)-phenolHCID 23321230HCID 23321230, compound

Product 1

HCID 23321221HCID 23321221, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To sodium hydride (0.53 g, 50% in oil, 11.0 mmol) in 40 ml of DMF, under N2 at 5°, is added, dropwise and with vigorous stirring, a solution of 4-(1-methylpropoxy)phenol (1.66 g, 10.0 mmol) in 10 ml of DMF. After the mixture is stirred at RT for 1 hour, a solution of 2-mesyloxymethyl-1,4-benzodioxin (2.70 g, 11.0 mmol) in 10 ml of DMF is slowly added. The resulting reaction mixture is stirred at RT for 48 hours and is then mixed with water and extracted with ether. The combined organic extracts are washed with water and with brine, dried and solvent removed and the product is purified by column chromatography to give 2-[4-(1-methylpropoxy)phenoxymethyl]-1,4-benzodioxin, MS m/e 315 (M+).

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred at RT for 48 hours
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed with water and with brine
  5. customdried
  6. customsolvent removed
  7. customthe product is purified by column chromatography

Sources & evidence

ORD record
ord-c4e935d5ba1b49e0b47ecfeac13b665f
Source dataset
uspto-grants-1986_05
Patent number
US04590282

Reaction notes

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