Sodium Sulfate → 3,3-Ethylenedioxy-5-(4-methoxyphenyl)-1-pentanol

HRID 256192Notes

Reaction equation

HRID 256192 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:18][C:19](OCC)=[O:20])=[CH:11][CH:10]=1.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:26]1[CH2:25][O:24][C:17]([CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)([CH2:18][CH2:19][OH:20])[O:27]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 13065016Ethyl 5-(4-methoxyphenyl)-3,3-ethylenedioxypentanoateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 130650173,3-Ethylenedioxy-5-(4-methoxyphenyl)-1-pentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 2 l. 3-necked r.b. flask equipped with mechanical stirrer, reflux condenser, and heating mantle was added 18 g. (0.474 mole) of LiAlH4 and 500 ml. of dry tetrahydrofuran at such a rate as to control vigorous reflux of reaction solution. 97 g. (0.33 mole) of ethyl 5-(4-methoxyphenyl)-3,3-ethylenedioxypentanoate in 100 ml. of dry tetrahydrofuran and added dropwise over a period of 40 minutes. The reaction mixture was stirred at room temperature for 30 minutes and refluxed for 2 hrs. Excess LiAlH4 was carefully decomposed with saturated Na2SO4 solution. The inorganic solid was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo leaving 84.6 g. of crude ketal alcohol.

Workup

  1. customflask equipped with mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureheating mantle
  4. additionwas added 18 g
  5. temperaturerefluxed for 2 hrs
  6. filtrationThe inorganic solid was filtered off
  7. washwashed with ethyl acetate
  8. concentrationThe filtrate was concentrated in vacuo
  9. customleaving 84.6 g

Sources & evidence

ORD record
ord-3af7e7a6efb0477095122dbc38dbf77c
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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