Water → HCID 86743097, compound

HRID 1493816Notes

Reaction equation

HRID 1493816 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 (25 g, 0.149 moles), 4-chlororesorcinol (18.26 g, 0.126 moles) and p-toluenesulfonic acid monohydrate (0.67 g, 0.0035 moles) were heated for 5.5 hours at 65°-70° C. in 37 mL 2-ethoxyethanol. The reaction mixture was diluted with 125 mL 2-ethoxyethanol and added dropwise to 1.5 L rapidly stirring H2O. The solid was collected by filtration, reslurried in 1 L H2O and refiltered. This process was repeated twice and the solid vacuum dried to yield 38.49 g. See Tables 1 and 2 for glass transition 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 solid vacuum dried
  3. customto yield 38.49 g
  4. dissolutionfor glass transition and alkaline dissolution data

Sources & evidence

ORD record
ord-b2450fd5f33b42ca84b4b076f3d15acf
Source dataset
uspto-grants-1991_06
Patent number
US05024921

Reaction notes

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