Water → 2-(7-Methyl-2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-ol

HRID 1065244Notes

Reaction equation

HRID 1065244 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][C:12](O)=[O:13])[O:7][C:6]=2[CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:13][CH2:12][CH2:11][CH:8]1[O:7][C:6]2[CH:15]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20540154(7-Methyl-2,3-dihydro-1,4-benzodioxin-2-yl)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 128506052-(7-Methyl-2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of 48.6 g of 2-(7-methyl-1,4-benzodioxan-2-yl)-acetic acid in the minimum amount of tetrahydrofuran is added dropwise at reflux rate to the stirred suspension of 13.4 g of lithium aluminum hydride in 200 ml of dry tetrahydrofuran. The mixture is refluxed overnight, cooled, and decomposed by the addition of 13.4 ml of water, 13.4 ml 15% aqueous sodium hydroxide and 40 ml of water. It is filtered, evaporated, the residue distilled in a molecular still, and the fraction boiling at 155°-165°/0.1 mmHg collected as colorless oil, to yield the 2-(2-hydroxyethyl)-7-methyl-1,4-benzodioxan.

Workup

  1. temperatureat reflux rate
  2. temperatureThe mixture is refluxed overnight
  3. temperaturecooled
  4. filtrationIt is filtered
  5. customevaporated
  6. distillationthe residue distilled in a molecular still, and the fraction boiling at 155°-165°/0.1 mmHg
  7. customcollected as colorless oil

Sources & evidence

ORD record
ord-7ed4a88225d44f7dbaab033015645078
Source dataset
uspto-grants-1982_05
Patent number
US04329348

Reaction notes

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