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

HRID 65959Notes

Reaction equation

HRID 65959 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 preparation of various new starting materials is illustrated as follows: 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 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 mm Hg collected as colorless oil, to yield the 2-(2-hydroxyethyl)-7-methyl-1,4-benzodioxan.

Workup

  1. customThe preparation of various new starting materials
  2. temperatureat reflux rate
  3. temperatureThe mixture is refluxed overnight
  4. temperaturecooled
  5. filtrationIt is filtered
  6. customevaporated
  7. distillationthe residue distilled in a molecular still, and the fraction boiling at 155°-165°/0.1 mm Hg
  8. customcollected as colorless oil

Sources & evidence

ORD record
ord-3b1967e667064c24a6989c023b21d039
Source dataset
uspto-grants-1978_12
Patent number
US04129655

Reaction notes

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