Water → 2-[Pentabromophenoxymethyl]-2-[2,4,6-tribromophenoxymethyl]-1,3-propanediol

HRID 597483Notes

Reaction equation

HRID 597483 reaction equation
[Br:1][C:2]1[CH:26]=[C:25]([Br:27])[CH:24]=[C:23]([Br:28])[C:3]=1[O:4][CH2:5][C:6]1([CH2:10][O:11][C:12]2[C:17]([Br:18])=[C:16]([Br:19])[C:15]([Br:20])=[C:14]([Br:21])[C:13]=2[Br:22])[CH2:9][O:8][CH2:7]1.O.S(=O)(=O)(O)[OH:31]>O1CCOCC1>[Br:18][C:17]1[C:12]([O:11][CH2:10][C:6]([CH2:5][O:4][C:3]2[C:2]([Br:1])=[CH:26][C:25]([Br:27])=[CH:24][C:23]=2[Br:28])([CH2:7][OH:8])[CH2:9][OH:31])=[C:13]([Br:22])[C:14]([Br:21])=[C:15]([Br:20])[C:16]=1[Br:19]

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 21445179HCID 21445179, compound

Product 1

HCID 214451802-[Pentabromophenoxymethyl]-2-[2,4,6-tribromophenoxymethyl]-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of the oxetane derivative of Example 2 (47.5 g., 0.053 moles), dioxane (290 ml.), water (10 ml.) and 1 g. of conc. sulfuric acid was stirred and refluxed 22 hours. The cooled reaction mixture was poured into 1.5 liters of water. A gummy solid formed which became crystalline when heated with dioxane. This product was recrystallized twice from dioxane, yielding 19.4 g. of the desired product which had a melting point of 184°-187° C.

Workup

  1. temperaturerefluxed 22 hours
  2. customThe cooled reaction mixture
  3. customA gummy solid formed which
  4. customThis product was recrystallized twice from dioxane
  5. customyielding 19.4 g

Sources & evidence

ORD record
ord-9a94cd0b65074bda8004e21d6f4813b2
Source dataset
uspto-grants-1977_03
Patent number
US04014855

Reaction notes

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