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Methanol → 1,3-Benzenediol, 4,4′-[(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)]bis-

HRID 1004539
Notes
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Reaction equation

HRID 1004539 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].O[CH2:10][C:11]1[C:16]([OH:17])=[C:15]([CH2:18]O)[CH:14]=[C:13]([CH3:20])[CH:12]=1.[OH2:21].[C:22]1(C)[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.C[OH:34]>>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[CH2:10][C:11]1[C:16]([OH:17])=[C:15]([CH2:18][C:22]2[CH:27]=[CH:26][C:25]([OH:21])=[CH:24][C:23]=2[OH:34])[CH:14]=[C:13]([CH3:20])[CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 887Methanol2×HCID 5054ResorcinolHCID 70392,6-Dimethylol-p-cresolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 150959471,3-Benzenediol, 4,4′-[(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)]bis-

Conditions

Temperature
86 °C

Procedure

To a 5 L 3-necked flask equipped with a reflux condenser was added 2.1 L of methanol, 754 g of resorcinol, 215 g of 2,6-bis(hydroxymethyl)-p-cresol and 4.38 g of p-toluenesulfonic acid monohydrate. The solution was then heated to and kept at reflux for 20 hours. A distillation head was added to the flask and 1.1 L of methanol removed by distillation over a one hour period. The reaction mixture was then slowly added over a 30 minute period using an addition funnel into 20 L of de-mineralized water. The precipitate was slurried for one hour and then collected using a Buchner funnel. The crude product was added to 6 L de-mineralized water, heated to 85-87° C. and slurried for 20 minutes at this temperature. The suspension was vacuum filtered while at 85° C. and the filtrate allowed to cool to ambient temperature overnight. The filtrant was again extracted with 3.0 L of de-mineralized water for 20 minutes at 85° C., the mixture was vacuum filtered and cooled. The precipitates from the filtrates were collected on a Buchner and vacuum oven dried at 100° C. A combined yield of 158 g was obtained having a purity of about 91 % as determined by HPLC analysis.

Workup

  1. customTo a 5 L 3-necked flask equipped with a reflux condenser
  2. temperatureThe solution was then heated to and
  3. temperatureat reflux for 20 hours
  4. customremoved by distillation over a one hour period
  5. additionThe reaction mixture was then slowly added over a 30 minute period
  6. customcollected
  7. additionThe crude product was added to 6 L de-mineralized water
  8. waitslurried for 20 minutes at this temperature
  9. filtrationfiltered while at 85° C.
  10. temperatureto cool to ambient temperature overnight
  11. extractionThe filtrant was again extracted with 3.0 L of de-mineralized water for 20 minutes at 85° C.
  12. filtrationfiltered
  13. temperaturecooled
  14. customThe precipitates from the filtrates
  15. customwere collected on a Buchner and vacuum oven
  16. customdried at 100° C
  17. customA combined yield of 158 g was obtained

Sources & evidence

ORD record
ord-516f18e30e7743819a5b5b7d29fb2810
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06051358

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes