Hydrochloric Acid → HCID 11301002, compound

HRID 1379310Notes

Reaction equation

HRID 1379310 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16]([OH:20])(=[O:19])[CH:17]=O.[ClH:21]>C(O)(=O)C.C(O)C>[C:11]([C:7]1[CH:8]=[C:9]([CH:17]([Cl:21])[C:16]([OH:20])=[O:19])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 11301002HCID 11301002, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

65 g of still wet (3,5-di-tert-butyl-4-hydroxy-phenyl)-chloroacetic acid are prepared from 41.2 g (0.2 mol) of 2,6-di-tert-butylphenol, 35.4 g (0.24 mol) of 50% aqueous glyoxylic acid and 44 g of hydrogen chloride in 200 ml of acetic acid as described in Example 2A. This acid is dissolved in 200 ml of absolute ethanol and allowed to stand overnight. The solvent is then evaporated in vacuo, 1.0 g of p-toluenesulfonic acid is added, followed by another 200 ml of absolute ethanol. The mixture is then heated for three hours, and the ethanol is then evaporated. The residue is then stirred at 0.1 mm Hg vacuum with the bath temperature slowly increasing up to 180° C. The title compound distills at a temperature between about 140°-160° C. as a viscous orange liquid in a yield of 27g.

Workup

  1. customThe solvent is then evaporated in vacuo, 1.0 g of p-toluenesulfonic acid
  2. additionis added
  3. temperatureThe mixture is then heated for three hours
  4. customthe ethanol is then evaporated
  5. distillationThe title compound distills at a temperature between about 140°-160° C. as a viscous orange liquid in a yield of 27g

Sources & evidence

ORD record
ord-65ea63401fde4b889f88892ce823200d
Source dataset
uspto-grants-1997_09
Patent number
US05670692

Reaction notes

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