Ethylene Glycol → HCID 20306076, compound

HRID 1732324Notes

Reaction equation

HRID 1732324 reaction equation
[Cl:1][C:2]1[C:12]([C:13](=[O:19])[C:14]2[S:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:5]2[CH2:6][CH:7]([CH:9]=[O:10])[O:8][C:4]=2[C:3]=1[Cl:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:32](O)[CH2:33][OH:34]>C1C=CC=CC=1.O>[CH2:33]1[O:34][CH:9]([CH:7]2[CH2:6][C:5]3[CH:11]=[C:12]([C:13](=[O:19])[C:14]4[S:18][CH:17]=[CH:16][CH:15]=4)[C:2]([Cl:1])=[C:3]([Cl:20])[C:4]=3[O:8]2)[O:10][CH2:32]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 12747909HCID 12747909, compound

Product 1

HCID 20306076HCID 20306076, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A benzene mixture (250 ml.) containing 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxaldehyde (3.2 g., 0.01 mole), p-toluenesulfonic acid (0.2 g.) and ethyleneglycol (15 ml.) is heated under reflux for three hours. The water formed in the reaction is co-distilled with the benzene and is removed by a Dean-Stark apparatus. After three hours, the reaction mixture is cooled, washed twice with dilute sodium bicarbonate (2×50 ml.) once with water (50 ml.) and dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give the 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxaldehyde ethyleneacetal.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for three hours
  3. customis removed by a Dean-Stark apparatus
  4. temperaturethe reaction mixture is cooled
  5. washwashed twice with dilute sodium bicarbonate (2×50 ml.) once with water (50 ml.)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-cafc78b2d5104f15aed879e317257a6f
Source dataset
uspto-grants-1980_12
Patent number
US04237144

Reaction notes

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