Acetic Acid → 4,4'-Hexylidenebisphenol

HRID 979276Notes

Reaction equation

HRID 979276 reaction equation
CO[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=CC=[CH:17][C:16]=1OC.Br.[C:24]([OH:27])(=O)[CH3:25].[OH2:28]>>[OH:28][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:25][C:24]([OH:27])=[CH:17][CH:16]=2)=[CH:3][CH:8]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 10518203HCID 10518203, compound

Product 1

HCID 904814,4'-HexylidenebisphenolYield 97.9%

Procedure

64.0 g (0.21 mole) of 1,6-bis(methoxyphenyl)hexane, 107.4 g of 48% hydrobromic acid and 281.2 g of pure acetic acid are put into a flask and the thick suspension is slowly heated to gentle reflux. The clear solution so obtained is then refluxed overnight. After cooling to room temperature, the slightly brownish red solution is stirred into 3 liters of water. The precipitate is isolated by filtration, washed with water until neutral and dried in vacuo at 70°-80° C., affording 55.6 g (97.9% of theory) of 1,6-bis(4-hydroxyphenyl)hexane with a melting point of 143°-144° C.

Workup

  1. temperaturethe thick suspension is slowly heated to gentle reflux
  2. customThe clear solution so obtained
  3. temperatureis then refluxed overnight
  4. customThe precipitate is isolated by filtration
  5. washwashed with water until neutral and
  6. customdried in vacuo at 70°-80° C.

Sources & evidence

ORD record
ord-63ae900cb858463bac0dbd2167ebfcb0
Source dataset
uspto-grants-1987_05
Patent number
US04667010

Reaction notes

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