Hydrochloric Acid → HCID 118689796, compound

HRID 2209320Notes

Reaction equation

HRID 2209320 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]=[CH2:30])=[CH:23][CH:22]=2)([CH3:20])[CH2:12][CH2:13][C:14](OCC=C)=[O:15])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].O1CCCC1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][CH:7]=2)([CH3:20])[CH2:12][CH2:13][CH2:14][OH:15])=[CH:22][CH:23]=1)[CH:29]=[CH2:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 118689797HCID 118689797, compound

Product 1

HCID 118689796HCID 118689796, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 5-L flask equipped with a stirrer, thermometer, and nitrogen purging line was charged with 655 g of allyl 4,4-bis(4-allyloxyphenyl)pentanoate and 1,310 g of tetrahydrofuran in a nitrogen atmosphere. Under ice cooling, 605 g of 70 wt % toluene solution of sodium bis(2-methoxyethoxy)aluminumhydride was added dropwise to the solution, followed by stirring at room temperature for 3 hours. Under ice cooling, 1,526 g of 10 wt % hydrochloric acid aqueous solution was added dropwise to quench the reaction. To the reaction solution were added 250 g of ethyl acetate and 750 g of toluene. An organic layer was taken out and washed three times with 500 g of water. The solvent was distilled off from the organic layer, and the residue was dissolved in 1,000 g of toluene, which was sequentially washed with five 300-g portions of 4 wt % sodium hydroxide aqueous solution, 330 g of 2 wt % hydrochloric acid aqueous solution, and four 300-g portions of water. Thereafter, the solvent was distilled off from the organic layer, obtaining 555 g of 4,4-bis(4-allyloxyphenyl)pentanol in crude form.

Workup

  1. customA 5-L flask equipped with a stirrer
  2. customto quench
  3. customthe reaction
  4. washwashed three times with 500 g of water
  5. distillationThe solvent was distilled off from the organic layer
  6. dissolutionthe residue was dissolved in 1,000 g of toluene
  7. washwhich was sequentially washed with five 300-g portions of 4 wt % sodium hydroxide aqueous solution, 330 g of 2 wt % hydrochloric acid aqueous solution, and four 300-g portions of water
  8. distillationThereafter, the solvent was distilled off from the organic layer

Sources & evidence

ORD record
ord-70556e565a814db6b774c12be14fa74f
Source dataset
uspto-grants-2016_06
Patent number
US09377689B2

Reaction notes

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