Hydrochloric Acid → HCID 19022457, compound

HRID 1198714Notes

Reaction equation

HRID 1198714 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([C:15]([C:18]2[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:19]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:17])[CH3:16])[CH:4]=1.B(Br)(Br)Br.[OH-].[Na+].[B].Cl>C(OCC)(=O)C.C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([C:15]([C:18]2[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:19]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:17])[CH3:16])[CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 5462311BoronHCID 54269027HCID 54269027, compound

Product 1

HCID 19022457HCID 19022457, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.21 grams (12.8 mmol.) of 2,2-bis(4-methoxybiphenylyl) propane and 6.30 grams (25.5 mmol.) of boron tribromide in 150 ml. of methylene chloride was stirred at room temperature in a nitrogen atmosphere for 18 hours, after which 50 ml. of 10% aqueous sodium hydroxide solution was cautiously added to hydrolyze boron compounds. After 1/2 hour, the mixture was diluted with an equal volume of ethyl acetate and acidified by the addition of 10% aqueous hydrochloric acid solution. The organic phase was separated, dried over magnesium sulfate and concentrated to give the crude product as yellow flakes. It was eluted through a plug of silica gel and recrystallized from chlorobenzene, to give a crude yield of 2.58 grams (53% of theoretical) of the desired 2,2-bis(4-hydroxybiphenylyl) propane as light tan crystals. Residual color was removed by refluxing for 48 hours in a solution of 2 grams of potassium hydroxide in 30 ml. each of tetrahydrofuran and methanol, followed by flash chromatography over silica gel with a mixture of ethyl acetate and hexane, to give fine white needles with a melting point of 237°-239° C.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give the crude product as yellow flakes
  5. washIt was eluted through a plug of silica gel
  6. customrecrystallized from chlorobenzene

Sources & evidence

ORD record
ord-fd8168b943e342b9aae04ccc57810ee3
Source dataset
uspto-grants-1994_01
Patent number
US05281689

Reaction notes

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