Water → HCID 86743097, compound

HRID 1904183Notes

Reaction equation

HRID 1904183 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:10][OH:11])[CH:6]=[C:5]([CH3:12])[CH:4]=1.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1[OH:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(OCCO)C>[OH:11][CH2:10][C:7]1[C:8]([OH:9])=[C:3]([CH2:2][OH:1])[CH:4]=[C:5]([CH3:12])[CH:6]=1.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1[OH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 17314-ChlororesorcinolHCID 70392,6-Dimethylol-p-cresolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86743097HCID 86743097, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent2×

Procedure

2,6-Bis(hydroxymethyl)-p-cresol (30 g, 0.178 moles), 4-chlororesorcinol (27.07 g, 0.187 moles) and p-toluenesulfonic acid monohydrate (0.8 g, 0.0042 moles) were heated at 87°-90° C. for four hours in 60 mL of stirred 2-ethoxyethanol. The reaction mixture was diluted with 250 mL 2-ethoxyethanol and added dropwise to 2.4 L of stirred H2O. The solid was collected by filtration, reslurried in 400 mL H2O, and stirred overnight. The polymer was again collected, reslurried, and filtered. The reslurrying operation was repeated twice more. The polymer was vacuum dried to yield 50.33 g. See Tables 1 and 2 for glass transition temperature and alkaline dissolution data. The ortho-, ortho-linkages of the alternating copolymers and the terminal groups were identified by 13C NMR analysis.

Workup

  1. filtrationThe solid was collected by filtration
  2. customThe polymer was again collected
  3. filtrationfiltered
  4. customdried
  5. customto yield 50.33 g
  6. dissolutionfor glass transition temperature and alkaline dissolution data

Sources & evidence

ORD record
ord-b7fd2af3dd204f87bf5b4fcba339c3ac
Source dataset
uspto-grants-1989_06
Patent number
US04837121

Reaction notes

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