3-Methoxyphenol → HCID 14415640, compound

HRID 1760138Notes

Reaction equation

HRID 1760138 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=C(O)[CH:6]=[CH:7][CH:8]=1.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH:13]=[CH2:14].[OH-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C.O>[CH3:10][O:11][CH:12]1[CH2:13][CH2:14][C:6]2[C:16](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O:15]1

Participants

7

Reactant 3

HCID 90073-MethoxyphenolHCID 14798Sodium HydroxideHCID 80145Acrolein dimethyl acetal

Product 1

HCID 14415640HCID 14415640, compoundYield 34.5%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A 500-milliliter flask fitted with a dropping funnel was charged with 12.4 g of 3-methoxyphenol, 0.2 g of p-toluenesulfonic acid monohydrate and 100 ml of diethyl ether for dissolution, and the mixture was cooled with ice. To this solution was slowly added dropwise 14.3 g of acrolein dimethyl acetal under room temperature. After the dropwise addition, the solution was stirred for 3 hours while being cooled with ice. The reaction solution was alkalized with the addition of 5 ml of a 5% sodium hydroxide aqueous solution and 30 ml of water. Subsequently, 200 ml of diethyl ether was added thereto for extraction. Thus obtained organic layer was washed with 30 ml of water, the diethyl ether was removed by distillation in vacuo therefrom, and the resulting residue was purified by distillation to obtain 6.7 g of a colorless liquid (yield 32%).

Workup

  1. customA 500-milliliter flask fitted with a dropping funnel
  2. temperaturethe mixture was cooled with ice
  3. additionAfter the dropwise addition
  4. temperaturewhile being cooled with ice
  5. extractionfor extraction
  6. washThus obtained organic layer was washed with 30 ml of water
  7. customthe diethyl ether was removed by distillation in vacuo
  8. distillationthe resulting residue was purified by distillation

Sources & evidence

ORD record
ord-8be8623b8f474a35963bda709a3fcdc9
Source dataset
uspto-grants-2005_01
Patent number
US06841183B2

Reaction notes

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