Ethylene Glycol → beta-Hydroxyethyl 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboxylate

HRID 894194Notes

Reaction equation

HRID 894194 reaction equation
Cl[C:2]([C:4]1[CH:19]=[CH:18][C:7]2[O:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[C:12](=[O:13])[C:6]=2[CH:5]=1)=[O:3].[CH2:20]([OH:23])[CH2:21][OH:22]>C(Cl)Cl>[O:13]=[C:12]1[C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[CH2:9][O:8][C:7]2[CH:18]=[CH:19][C:4]([C:2]([O:22][CH2:21][CH2:20][OH:23])=[O:3])=[CH:5][C:6]1=2

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 134560052-Chlorocarbonyl-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 21162728beta-Hydroxyethyl 6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.0 gm of 2-chlorocarbonyl-6,11-dihydro-11-oxo-dibenz[b,e]oxepin in 50 cc of methylene chloride, add 3 gm of ethylene glycol and stir the mixture for 18 hours at room temperature. Distill off the solvent and excess ethylene glycol under high vacuum (0.1 mm). Chromatograph the residue on a silica gel column (100 gm), eluting with 10% ethyl acetate in benzene to obtain the title product.

Workup

  1. distillationDistill off the solvent and excess ethylene glycol under high vacuum (0.1 mm)
  2. washChromatograph the residue on a silica gel column (100 gm), eluting with 10% ethyl acetate in benzene

Sources & evidence

ORD record
ord-e3c7119cebe54ca58ea921f2e1b8be8e
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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