Ethylene Glycol → HCID 23286119, compound

HRID 367337Notes

Reaction equation

HRID 367337 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:8]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C([O-])([O-])OC.[CH2:28](O)[CH2:29][OH:30].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C(N(CC)CC)C>[CH2:16]([O:15][C:7]1[CH:6]=[CH:5][C:4]([C:1]2([CH3:2])[O:30][CH2:29][CH2:28][O:3]2)=[CH:9][C:8]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 11022895HCID 11022895, compoundHCID 53629101Methylorthoformate

Product 1

HCID 23286119HCID 23286119, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methyl 2-(5-acetyl-2-benzyloxyphenyl)acetate (9.0 g), 18 ml of methyl orthoformate and 18 ml of ethylene glycol were dissolved in 300 ml of methylene chloride, 60 mg of p-toluenesulfonic acid monohydrate was added to the solution, and the mixture was heated under reflux for 12 hours. After cooling, 0.14 ml of triethylamine was added to the reaction solution and the mixture was stirred for 15 minutes. The reaction solution was partially purified by silica gel flash column chromatography (eluent: methylene chloride) and then further purified by silica gel medium pressure liquid column chromatography (eluent: hexane/diethyl ether=3/2) to give 9.2 g of methyl 2-[2-benzyloxy-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]acetate in an oily form.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. customThe reaction solution was partially purified by silica gel flash column chromatography (eluent: methylene chloride)
  5. customfurther purified by silica gel medium pressure liquid column chromatography (eluent: hexane/diethyl ether=3/2)

Sources & evidence

ORD record
ord-25d2d9ca8f00440a99627f6619a2157c
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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