Sodium Hydroxide → 2-(7-Methoxy-2H-1,3-benzodioxol-5-yl)ethan-1-ol

HRID 1253102Notes

Reaction equation

HRID 1253102 reaction equation
[Li].[H-].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15](O)=[O:16])[CH:8]=[C:9]2[O:13][CH2:12][O:11][C:10]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)C.O.O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:14][CH2:15][OH:16])[CH:8]=[C:9]2[O:13][CH2:12][O:11][C:10]=12

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 3028194LithiumHCID 139234077-Methoxy-1,3-benzodioxole-5-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 139234082-(7-Methoxy-2H-1,3-benzodioxol-5-yl)ethan-1-olYield 68.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7.30 g (0.192 mol) of lithium alminium hydride was added to 270 ml of anhydrous tetrahydrofuran, and to this solution was added portionwise 33.68 g of 3-methoxy-4,5-methylenedioxyphenylacetic acid (2) with stirring under water-cooling. The mixture was stirred at room temperature for one hour, then added with 2.0 g (53 mmol) of lithium aluminium hydride and further stirred for one hour. The reaction mixture, while being cooled in an ice bath, was added portionwise with a solution of 9.3 ml of water and 10 ml of tetrahydrofuran and then further added portionwise with 9.3 ml of 15% sodium hydroxide aqueous solution. The resulting mixture was further added with 27.9 ml of water and then 500 ml of ethyl ether followed by stirring for 30 minutes. The deposited salt was filtered out and washed with ethyl ether. The filtrate and the ethyl ether used for washing were joined and concentrated under reduced pressure, and the residual oil was distilled in vacuo to obtain 19.09 g of 2-(3-methoxy-4,5-methylenedioxyphenyl)ethyl alcohol (3) as an oil. Boiling point: 140°-142° C./ 1 mmHg: yield 68.4%.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for one hour
  3. stirringfurther stirred for one hour
  4. temperatureThe reaction mixture, while being cooled in an ice bath
  5. stirringby stirring for 30 minutes
  6. filtrationThe deposited salt was filtered out
  7. washwashed with ethyl ether
  8. washfor washing
  9. concentrationconcentrated under reduced pressure
  10. distillationthe residual oil was distilled in vacuo

Sources & evidence

ORD record
ord-3ec967aef1ff4542b028f04c6e3f450f
Source dataset
uspto-grants-1988_05
Patent number
US04746747

Reaction notes

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