Bis(4-hydroxyphenyl)methane → Bis(p-(3-butoxy-2-hydroxypropyloxy)phenyl)methane

HRID 894480

Reaction equation

HRID 894480 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[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>[CH2:21]([O:20][CH2:16][CH:17]([OH:19])[CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:18][CH:17]([OH:19])[CH2:16][O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

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

Product 1

HCID 20574263Bis(p-(3-butoxy-2-hydroxypropyloxy)phenyl)methane

Reagents, catalysts & solvents 1

HCID 5963Benzyltrimethylammonium chlorideCatalyst

Conditions

Temperature
100 °C

Procedure

Bis(p-hydroxyphenyl)methane (303 g; 1.5 moles), butyl glycidyl ether of epoxide content 7.45 equiv./kg (402.7 g; 6 equiv.), and benzyltrimethylammonium chloride (3 g) were stirred together and heated to 100° C., at which temperature an exothermic reaction commenced. The mixture was kept at 120° C. by moderate cooling and then, when the temperature of the mixture began to fall, heating was resumed, keeping the temperature at 120° C. for 1 hour and 150° C. for 4 hours. The mixture was cooled, and its epoxide content was found to be 0.1 equiv./kg, indicating that the reaction was virtually complete.

Workup

  1. customan exothermic reaction
  2. customwas kept at 120° C.
  3. temperatureby moderate cooling
  4. temperatureheating
  5. customat 120° C.
  6. customfor 1 hour
  7. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-7ca643d425bc45448341e50a01dee08e
Source dataset
uspto-grants-1981_08
Patent number
US04284574

Linked notes

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