Hydrochloric Acid → 3,5-Diethyl-4-(4-(2,2-diethoxyethoxy)butyloxy)phenol

HRID 369687Notes

Reaction equation

HRID 369687 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([O:25]C(=O)C2C=CC=CC=2)[CH:6]=[C:7]([CH2:23][CH3:24])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:2].[OH-].[K+].Cl>CO.O>[CH2:23]([C:7]1[CH:6]=[C:5]([OH:25])[CH:4]=[C:3]([CH2:1][CH3:2])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 184296493,5-Diethyl-1-benzoyloxy-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene

Product 1

HCID 184295323,5-Diethyl-4-(4-(2,2-diethoxyethoxy)butyloxy)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 31.0 g of 3,5-diethyl-1-benzoyloxy-4-(4-(2,2-diethoxyethoxy)butyloxy)benzene dissolved in 100 ml of methanol added a solution of 5.1 g of potassium hydroxide dissolved in 25 g of water. After stirring at room temperature for 1 hour, the reaction mixture was acidified by the addition of diluted hydrochloric acid and then concentrated. Water was added to the residue, which was extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over magnesium sulfate and then concentrated. The residue was subjected to silica gel chromatography, which afforded 0.60 g of 3,5-diethyl-4-(4-(2,2-diethoxyethoxy)butyloxy)phenol (yield, 94%), nD25.0 1.4890.

Workup

  1. concentrationconcentrated
  2. additionWater was added to the residue, which
  3. extractionwas extracted twice with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f4f8b37ba5f4b04aeeca82ffbfaecc0
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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