Hydrochloric Acid → 2,20-Dichloro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13]-pentaoxacyclo-octadecin

HRID 2049105Notes

Reaction equation

HRID 2049105 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29]Cl.[OH-].[Na+].Cl>CCCCO>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[O:17][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:1][C:2]3[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=3[CH2:9][C:10]=2[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3037DichlorophenHCID 14798Sodium HydroxideHCID 611871,1'-Oxybis[2-(2-chloroethoxy)ethane]

Product 1

HCID 203457582,20-Dichloro-6,7,9,10,12,13,15,16-octahydro-22H-dibenzo[n,q][1,4,7,10,13]-pentaoxacyclo-octadecinYield 23.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

10 g (0.037 mole) bis(2-hydroxy-5-chlorophenyl)-methane and 8.6 g (0.037 mole) 1,11-dichloro-3,6,9-trioxaundecane are dissolved in 100 ml n-BuOH. To this is added 6.5 g 50% aqueous sodium hydroxide. The resulting solution is heated to reflux for 15 hours, acidified with ethereal HCl, and solvent stripped in vacuo. The resulting gum is chromatographed on Neutral Alumina IV, eluting with ether/ethyl acetate. Appropriate fractions are collected, combined and recrystallized from methanol to yield 3.65 g white crystalline solid; m.p. 143.5°-144°. Yield: 23%.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for 15 hours
  3. customThe resulting gum is chromatographed on Neutral Alumina IV
  4. washeluting with ether/ethyl acetate
  5. customAppropriate fractions are collected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fcb16beadb9d4d88b428fe0f5ef73338
Source dataset
uspto-grants-1980_04
Patent number
US04196250

Reaction notes

Loading…