Methanesulfonic Acid → 1-(2,2-Dimethoxyethyl)-4-(octyloxy)benzene

HRID 128780Notes

Reaction equation

HRID 128780 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1.CS(O)(=O)=O.[C:25](=O)(O)[O-:26].[Na+]>CO>[CH3:1][O:2][CH:3]([O:26][CH3:25])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 537755121-(2-Methoxyethenyl)-4-(octyloxy)benzene

Product 1

HCID 152852921-(2,2-Dimethoxyethyl)-4-(octyloxy)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-methoxyethenyl)-4-(octyloxy)benzene (3.67 g) and methanesulfonic acid (0.5 ml) in methanol (30 ml) is refluxed for 30 min, cooled, and neutralized with 1.0N aqueous sodium bicarbonate (10 ml). The mixture is evaporated in vacuo, and the residue dissolved in ether, dried with sodium sulfate, filtered, and evaporated to leave 1-(2,2-dimethoxyethyl)-4-(octyloxy)benzene as a colorless oil. This acetal may be used directly in step C below (as in example 2). Alternatively, the acetal is dissolved in a 1:1 mixture of THF and 3N hydrochloric acid, refluxed for one hour, and cooled. The mixture is extracted with dichloromethane, and without drying the dichloromethane extracts are concentrated to provide crude 4-(octyloxy)phenylacetaldehyde as an oil.

Workup

  1. temperaturecooled
  2. customThe mixture is evaporated in vacuo
  3. dissolutionthe residue dissolved in ether
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4a55b3da09384a84ad5db676b28b08f9
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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