Hydrochloric Acid → {3,5-Bis[(prop-2-en-1-yl)oxy]phenyl}methanol

HRID 383058Notes

Reaction equation

HRID 383058 reaction equation
C([C:4]1[C:12]([O:13][CH2:14][CH:15]=[CH2:16])=[CH:11][C:10]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:9][C:5]=1[C:6]([O-])=[O:7])=CC.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>C(OCC)C.O>[CH2:18]([O:17][C:10]1[CH:9]=[C:5]([CH:4]=[C:12]([O:13][CH2:14][CH:15]=[CH2:16])[CH:11]=1)[CH2:6][OH:7])[CH:19]=[CH2:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 131722943HCID 131722943, compound

Product 1

HCID 15831649{3,5-Bis[(prop-2-en-1-yl)oxy]phenyl}methanolYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2-Propenyl-3,5-bis-(2-propenyloxy)-benzoate (23.1 g, 84.2 mmol) was dissolved in dry diethyl ether (250 ml) and added dropwise at 0° C. to a suspension of lithium aluminium hydride (3.45 g, 91.0 mmol) in dry diethyl ether (200 ml). The mixture was stirred at room temperature for 16 h and ethyl acetate (5 ml) was added slowly followed by water (10 ml) and diluted aqueous hydrochloric acid (2 M, 4 ml) to bring pH to 4. The phases were separated and the aqueous phase was extracted with diethyl ether (50 ml). The combined organic phases washed with water (50 ml), dried (Na2SO4), and the solvent was evaporated to give 18.4 g (99%) of the product as a colorless oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with diethyl ether (50 ml)
  3. washThe combined organic phases washed with water (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9b79fd77dc5b49179168064d5a8a8311
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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