6-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenol → HCID 86734283, compound

HRID 1973711Notes

Reaction equation

HRID 1973711 reaction equation
[C:1]([O-:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.[C:13]([C:17]1[CH:24]=[C:23]([CH3:25])[C:20]([CH2:21]Cl)=[C:19]([CH3:26])[C:18]=1[OH:27])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:1]([O:12][CH2:21][C:20]1[C:23]([CH3:25])=[CH:24][C:17]([C:13]([CH3:14])([CH3:15])[CH3:16])=[C:18]([OH:27])[C:19]=1[CH3:26])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:21][C:20]2[C:23]([CH3:25])=[CH:24][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[C:18]([OH:27])[C:19]=2[CH3:26])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 901316-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenolHCID 1542691,4-Benzenedicarboxylate

Product 1

HCID 86734283HCID 86734283, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of disocium terephthalate, 16.5 g. (0.08 mole) and 4-tert.-butyl-3-hydroxy-2,6-dimethylbenzyl chloride, 35.7 g. (0.158 mole) in 200 ml. of dimethylformamide was heated at reflux for 18 hours. The salt was then filtered off, and the filtrate poured into 400 ml. of water. The resulting brown gum was dissolved in 50 ml. of methanol and reprecipitated by addition of water. This procedure was repeated to give 18.9 g. (44%) of product, m.p. 227°-230° C. Anal. calc'd. for C34H42O6 : C=74.67, H=7.75; found: C=74.03, H=7.75.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe salt was then filtered off
  3. additionthe filtrate poured into 400 ml
  4. dissolutionThe resulting brown gum was dissolved in 50 ml
  5. customof methanol and reprecipitated by addition of water
  6. customto give 18.9 g

Sources & evidence

ORD record
ord-9de5e31d2e4c46d7800e5d0abfcc2955
Source dataset
uspto-grants-1976_12
Patent number
US03998863

Reaction notes

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