Ethylene Glycol → HCID 23286119, compound

HRID 369367Notes

Reaction equation

HRID 369367 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>ClCCl.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), methyl orthoformate (18 ml) and ethylene glycol (18 ml) were dissolved in dichloromethane (300 ml), and p-toluenesulfonic acid monohydrate (60 mg) was added to the solution, then the resulting mixture was heated under reflux for 12 hours. After cooling, triethylamine (0.14 ml) was added to the reaction mixture, and the resulting mixture was stirred for 15 minutes. Rough purification by flash column chromatography on silica gel (eluent: dichloromethane) and sequential purification by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=3/2) of the reaction mixture gave methyl 2-[2-benzyloxy-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]acetate (9.2 g) as an oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. customRough purification by flash column chromatography
  5. customon silica gel (eluent: dichloromethane) and sequential purification by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=3/2) of the reaction mixture

Sources & evidence

ORD record
ord-651c70f2456345f7bdef4e2bc06aad8d
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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