Hydrogen Bromide → 4,4'-Pentane-1,5-diyldiphenol

HRID 979064Notes

Reaction equation

HRID 979064 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 132200991,5-Bis(4-methoxyphenyl)pentane

Product 1

HCID 2578384,4'-Pentane-1,5-diyldiphenolYield 98.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,5-bis(4-methoxyphenyl)pentane of Example 8 (60 g, 0.21 mole), 150 ml of hydrobromic acid (47%) and 200 ml of glacial acetic acid was refluxed for 4.5 hours. It was concentrated to a thick liquid, dissolved in ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 53.0 g of a thick oil. NMR and TLC confirmed the structure.

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. concentrationIt was concentrated to a thick liquid
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-47aedacbc99c477e82b8f1a0d7198eb2
Source dataset
uspto-grants-1987_05
Patent number
US04666909

Reaction notes

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