1-Propanol → n-Propyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate

HRID 2082846Notes

Reaction equation

HRID 2082846 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2.[CH2:21](O)[CH2:22][CH3:23].S(=O)(=O)(O)O>CCOCC>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:20][CH2:21][CH2:22][CH3:23])=[O:19])=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 41448Isoxepac

Product 1

HCID 12330025n-Propyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 7.0 g of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid, Example 2, 175 ml of n-propanol, and 4.6 ml of concentrated sulfuric acid is refluxed for 17 hours. The reaction mixture is permitted to cool and the solvent removed leaving an oil. The oil is dissolved in ether and washed successively with water, a 5% sodium hydroxide solution and water and dried and the ether removed to give a yellow oil which crystallizes upon standing. The solid is dried on a porous plate resulting in an off-white solid, mp 30°-32° C, of n-propyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate.

Workup

  1. temperatureis refluxed for 17 hours
  2. temperatureto cool
  3. customthe solvent removed
  4. customleaving an oil
  5. washwashed successively with water
  6. dry with materiala 5% sodium hydroxide solution and water and dried
  7. customthe ether removed
  8. customto give a yellow oil which
  9. customcrystallizes
  10. customThe solid is dried on a porous plate

Sources & evidence

ORD record
ord-6df799ac9efa434da596cca40745f1cc
Source dataset
uspto-grants-1978_04
Patent number
US04082850

Reaction notes

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