3,4-dihydro-2H-pyran → Tetrabromobisphenol A bis-tetrahydropyranyl ether

HRID 1653621Notes

Reaction equation

HRID 1653621 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])[C:3]=1[Br:21].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.[C:28](=[O:31])([O-])[O-].[K+].[K+]>C1COCC1>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]1[O:8][C:7]1[C:2]([Br:1])=[C:3]([Br:21])[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH:4]3[CH2:3][CH2:2][CH2:7][CH2:28][O:31]3)=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[C:5]([Br:10])[C:6]=1[Br:9]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 542409822,3,5,6-Tetrabromo-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Product 1

HCID 54165907Tetrabromobisphenol A bis-tetrahydropyranyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

56.6 g of tetrabromobisphenol A are dissolved in 50 ml of THF. After addition of 17.5 g of dihydropyran and 0.25 g of Amberlyst, the mixture is refluxed for 3 hours, cooled, neutralized by addition of 5 g of potassium carbonate, stirred for a further hour, filtered and evaporated to dryness: oil. NMR: 7.27 ppm (arom.), 6.0 ppm (t, acetal), 1.57 ppm (methyl).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-eeaa11de1f61461d955e69eb68523400
Source dataset
uspto-grants-1995_04
Patent number
US05403697

Reaction notes

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