Ethylene Glycol → HCID 20542010, compound

HRID 1863478Notes

Reaction equation

HRID 1863478 reaction equation
[OH:1][CH:2]=[C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:15][CH3:16])[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4]1=[O:17].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[CH2:19]1[O:20][CH:2]([CH:3]2[CH2:12][CH2:11][C:10]3[C:5](=[C:6]([O:15][CH3:16])[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=3)[C:4]2=[O:17])[O:1][CH2:18]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 70553603HCID 70553603, compound

Product 1

HCID 20542010HCID 20542010, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 5.73 g. of 2-hydroxymethylene-6,8-dimethoxy-1-tetralone, 2.23 g. of ethylene glycol and 100 mg. of p-toluenesulfonic acid in 25 ml. of benzene was heated at reflux two hours under a Dean-Stark water separator. The mixture was filtered, the filtrate was washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo to give 1,2,3,4-tetrahydro-6,8-dimethoxy-1-oxo-2-naphthaldehyde ethylene acetal which was converted directly to 1,2,3,4-tetrahydro-1-hydroxy-6,8-dimethoxy-2-naphthaldehyde ethylene acetal as described hereinabove in Example 155.

Workup

  1. additionA solution containing 5.73 g
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with saturated aqueous solutions of sodium bicarbonate and sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e56136a1259e4d6e9af793be5eabfc34
Source dataset
uspto-grants-1979_09
Patent number
US04169108

Reaction notes

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