Hydrochloric Acid → 4-(Hydroxymethyl)-5-[4-(tetradecyloxy)phenyl]-2-pentanone

HRID 235705Notes

Reaction equation

HRID 235705 reaction equation
[CH3:1][C:2]1([CH2:7][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=2)[CH2:9][OH:10])OCC[O:3]1.Cl>O1CCOCC1>[OH:10][CH2:9][CH:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=1)[CH2:7][C:2](=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 202193422-Methyl-beta-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanol

Product 1

HCID 202189924-(Hydroxymethyl)-5-[4-(tetradecyloxy)phenyl]-2-pentanoneYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of about 12.0 g of 2-methyl-β-[[4-(tetradecyloxy)phenyl]methyl]-1,3-dioxolane-2-propanol, about 50 ml of about 1N hydrochloric acid and about 300 ml of dioxane was stirred for about 3 hours. The dioxane was then removed, the residue diluted with water and extracted with ether. The ether extract was washed with saturated aqueous sodium bicarbonate, dried and the solvent removed, giving an oil, which crystallized on standing, giving about 10.5 g of the desired title compound.

Workup

  1. customThe dioxane was then removed
  2. additionthe residue diluted with water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with saturated aqueous sodium bicarbonate
  6. customdried
  7. customthe solvent removed
  8. customgiving an oil, which
  9. customcrystallized

Sources & evidence

ORD record
ord-c581cbdde6cf42c1a18133e6bf430f64
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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