Hydrochloric Acid → HCID 11301002, compound

HRID 1290282Notes

Reaction equation

HRID 1290282 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:18].[ClH:21].[C:22]1([CH3:28])[CH:27]=[CH:26]C=CC=1>C(O)(=O)C.C(O)CCC>[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].[C:11]([C:7]1[CH:8]=[C:9]([CH:17]([O:18][CH2:28][CH2:22][CH2:27][CH3:26])[C:16]([O:20][CH2:2][CH2:1][CH2:5][CH3:6])=[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 1140TolueneHCID 314052,6-Di-tert-butylphenol

Product 2

HCID 11301002HCID 11301002, compoundHCID 53992269HCID 53992269, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 2631-ButanolSolvent

Procedure

68 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-butyl-phenol, 35.4 g (0.24 mol) of 50% aqueous glyoxylic acid and 54 g of hydrogen chloride in 200 ml of acetic acid as described in Example 2 A. This acid is dissolved in 200 ml of absolute n-butanol and allowed to stand for three days. 25 ml of toluene are then added and the mixture is heated on the Dean-Stark trap for three hours. The solvents are then evaporated in vacuo to give 72.4 g of the crude n-butyl (3,5-di-tert-butyl-4-hydroxy-phenyl)-n-butoxyacetate as a slightly yellow viscous oil. 40.5 g (0.1 Mol) of this intermediate ester and 1.0 g of a dried FULCAT® 22B catalyst are stirred at 0.1 mm Hg vacuum with bath temperature slowly increasing up to 200° C. The title compound distills over between about 150°-170° C. as a viscous orange liquid in a yield of 24 g.

Workup

  1. temperaturethe mixture is heated on the Dean-Stark trap for three hours
  2. customThe solvents are then evaporated in vacuo

Sources & evidence

ORD record
ord-3721fb21c5654ea28a27ad3cf87fc207
Source dataset
uspto-grants-1998_05
Patent number
US05750765

Reaction notes

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