Hydrochloric Acid → HCID 20042847, compound

HRID 259384Notes

Reaction equation

HRID 259384 reaction equation
[OH-].[Na+].C1(C)C=CC=CC=1.[C:10]([C:14]1[CH:15]=[C:16]([CH:37]=[C:38]([C:41]([CH3:44])([CH3:43])[CH3:42])[C:39]=1[OH:40])[C:17]([O:19][C:20]1[C:28]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][C:23]([C:24]([O-:26])=[O:25])=[CH:22][C:21]=1[C:33]([CH3:36])([CH3:35])[CH3:34])=[O:18])([CH3:13])([CH3:12])[CH3:11].[Na+].Cl>CCOCC>[C:41]([C:38]1[CH:37]=[C:16]([CH:15]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:39]=1[OH:40])[C:17]([O:19][C:20]1[C:21]([C:33]([CH3:34])([CH3:35])[CH3:36])=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][C:28]=1[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:18])([CH3:42])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 23703018HCID 23703018, compound

Product 1

HCID 20042847HCID 20042847, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

450 ml of 2N sodium hydroxide were added to the toluene filtrate at room temperature and gradually heated to reflux. The reaction was heated at reflux for 41/2 hours. The reaction mixture was cooled to 0° to 5° C. by an ice-water bath whereupon a thick precipitate formed consisting of the intermediate sodium 4-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)-3,5-di-tert-butylbenzoate. 70 ml of concentrated aqueous hydrochloric acid was gradually added dropwise with cooling at 30° C. 150 ml of ether was added with stirring to the reaction mixture at 20° to 25° C. The aqueous phase was separated and the organic phase washed with two 100 ml portions of water. The separated organic phase was then dried over anhydrous sodium sulfate. The residue was isolated from the organic phase by evaporation of the solvent initially at about 20 mm Hg. pressure and finally at 0.5 mm Hg.

Workup

  1. temperaturegradually heated to reflux
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 41/2 hours
  4. temperatureThe reaction mixture was cooled to 0° to 5° C. by an ice-water bath whereupon a thick precipitate
  5. customformed
  6. customThe aqueous phase was separated
  7. washthe organic phase washed with two 100 ml portions of water
  8. dry with materialThe separated organic phase was then dried over anhydrous sodium sulfate
  9. customThe residue was isolated from the organic phase by evaporation of the solvent initially at about 20 mm Hg

Sources & evidence

ORD record
ord-1128ce3c788a487daaec36e9adeeec1c
Source dataset
uspto-grants-1977_07
Patent number
US04038249

Reaction notes

Loading…