Acetic Acid → 4,4'-Hexylidenebisphenol

HRID 1583552Notes

Reaction equation

HRID 1583552 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.Br.C(O)(=O)C>CCOCC>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 2292421-methoxy-4-[6-(4-methoxyphenyl)hexyl]benzene

Product 1

HCID 904814,4'-HexylidenebisphenolYield 77.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 40.0 g of 1,6-bis(4-methoxyphenyl)hexane of Example 2, 150 ml of HBr (48%) and 150 ml of glacial acetic acid was refluxed for 5 hours. It was concentrated by evaporation to give a dark brown semi-solid. This was dissolved in ether, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 28.0 g of dark brown semi-solid.

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationIt was concentrated by evaporation
  3. customto give a dark brown semi-solid
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-306741ee6cf9437ea36c09a414476cc1
Source dataset
uspto-grants-1985_11
Patent number
US04552876

Reaction notes

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