Ethylene Glycol → HCID 86734637, compound

HRID 328350Notes

Reaction equation

HRID 328350 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH2:12][C:11]1[C:6]2([CH2:18][C:19]#[N:20])[CH2:7][CH2:8][C:9](=[O:17])[CH:10]=1.C1C=CC=CC=1.[CH2:27](O)[CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.O>[CH2:27]1[CH2:28][O:29][C:9]2([CH2:8][CH2:7][C:6]3([CH2:18][C:19]#[N:20])[C:11](=[CH:12][CH2:13][C:14]4[C:5]3=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=4)[CH2:10]2)[O:17]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 21883250HCID 21883250, compound

Product 1

HCID 86734637HCID 86734637, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the crude enone III, benzene (2.5 l), ethylene glycol (150 ml) and p-toluenesulphonic acid (4.0 g) was refluxed with water separation (Dean-Stark trap) for 17 hrs. cooled and evaporatd at reduced pressure to approximately 500 ml. Dichloromethane (2.5 l) was added; the mixture worked up, the organic solution was evaporated to approximately 700 ml and diluted with ether (1.5l). The ketal IV was obtained in two crops as colorless needles (249 g, 80%); m.p. 174°-175° C.

Workup

  1. temperaturecooled
  2. customthe organic solution was evaporated to approximately 700 ml
  3. additiondiluted with ether (1.5l)

Sources & evidence

ORD record
ord-32b909f9bddf4dcc846dc288781ba617
Source dataset
uspto-grants-1977_04
Patent number
US04017497

Reaction notes

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