Methanol → HCID 15117887, compound

HRID 1957421Notes

Reaction equation

HRID 1957421 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:24]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:24])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 37812985-tert-Octylsalicylic Acid

Product 1

HCID 15117887HCID 15117887, compoundYield 92%

Procedure

A solution of 49.8 g (0.199 mol) of 2-hydroxy-5-(1,1,3,3-tetramethylbutyl)benzoic acid in 200 ml of methanol was heated to 50° C. and then treated dropwise with about 80 g of sulfuric acid at a rate to maintain the reaction under reflux. The reaction mixture was heated under reflux for an additional 11 hours, then cooled and partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, then with brine, dried over sodium sulfate and taken to dryness to give 48.6 g (92%) of methyl 2-hydroxy-5-(1,1,3,3-tetramethylbutyl)benzoate.

Workup

  1. temperatureto maintain
  2. customthe reaction
  3. temperatureunder reflux
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for an additional 11 hours
  6. temperaturecooled
  7. custompartitioned between water and ethyl acetate
  8. washThe organic layer was washed with saturated sodium bicarbonate
  9. dry with materialwith brine, dried over sodium sulfate

Sources & evidence

ORD record
ord-ca5ba51692544df68bd95268bee424aa
Source dataset
uspto-grants-1998_07
Patent number
US05783589

Reaction notes

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