Ethylene Glycol → 2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

HRID 616527

Reaction equation

HRID 616527 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8](CC#N)=[C:7]([CH3:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[OH-:17].[Na+].[CH2:19]([OH:22])[CH2:20]O>O>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:20][C:19]([OH:22])=[O:17])=[C:7]([CH3:15])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 1087564-tert-Butyl-3-hydroxy-2,6-xylylacetonitrile

Product 1

HCID 203459052-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

65.1 grams of the compound of Example 3 was added with stirring to a solution of 36 grams of sodium hydroxide in 40 ml of ethylene glycol and 66 ml of water. The reaction mixture became homogenous at about 116° to 117° and was heated at this temperature for 2 hours. The reaction mixture was cooled by the addition of chopped ice and cold water to the reaction mixture to make a total volume of one liter. After clarifying the reaction mixture by filtration, the filtrate was made acid with concentrated aqueous hydrochloric acid, yielding a white precipitate, which was filtered, washed with cold water and dried. The product was then treated with rapid stirring at 50° C with about 800 ml of 6% sodium bicarbonate solution until carbon dioxide evolution stopped. The turbid solution was filtered free of a white solid by-product. (A). The clarified filtrate was made acid with concentrated hydrochloric acid while cooling, and the resulting white precipitate filtered. After washing with hot water and drying the product was obtained as a white powder melting at 161° to 165°.

Workup

  1. custombecame homogenous at about 116° to 117°
  2. temperaturewas heated at this temperature for 2 hours
  3. filtrationby filtration
  4. customyielding a white precipitate, which
  5. filtrationwas filtered
  6. washwashed with cold water
  7. customdried
  8. additionThe product was then treated
  9. filtrationThe turbid solution was filtered free of a white solid by-product
  10. temperaturewhile cooling
  11. filtrationthe resulting white precipitate filtered
  12. washAfter washing with hot water
  13. customdrying the product

Sources & evidence

ORD record
ord-a87ac562427a47849c689a446715abb0
Source dataset
uspto-grants-1978_02
Patent number
US04075161

Linked notes

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