Bis(4-hydroxyphenyl)methane → bis(p-(2-Hydroxy-3-butoxypropyl)phenyl)methane

HRID 46796

Reaction equation

HRID 46796 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:16]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:17]1[O:19][CH2:18]1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[OH:19][CH:17]([CH2:16][O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:18][CH:17]([OH:19])[CH2:16][O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12111Bis(4-hydroxyphenyl)methaneHCID 17049Butyl glycidyl ether

Product 1

HCID 20385783bis(p-(2-Hydroxy-3-butoxypropyl)phenyl)methane

Reagents, catalysts & solvents 1

HCID 5963Benzyltrimethylammonium chlorideCatalyst

Procedure

bis(p-Hydroxyphenyl)methane (153 g; 67% pure, containing polynuclear homologues), butyl glycidyl ether (232.5 g), and benzyltrimethylammonium chloride (3.85 g) were stirred and heated slowly to 100°, when a mildly exothermic reaction commenced and the temperature rose to 110°. The mixture was kept at 110° for 41/2 hours, 120° for 1 hour, and 150° for 11/2 hours. The product had an epoxy value of 0.19 equiv./kg.

Workup

  1. temperatureheated slowly to 100°
  2. customrose to 110°
  3. customwas kept at 110° for 41
  4. custom2 hours, 120°
  5. customfor 1 hour
  6. custom150°
  7. custom2 hours

Sources & evidence

ORD record
ord-1bad6868e8ea4414aa9b3a4168ed2c51
Source dataset
uspto-grants-1979_11
Patent number
US04175173

Linked notes

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