gamma-Propanol → 4-(3-Hyd-roxypropyl)-2-t-butylphenol
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH2:18][OH:19])[CH:8]=[C:9](C(C)(C)C)[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH2:18][OH:19])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)-1-propanol (100 g, 0.38 mol) was dissolved in 500 ml of trifluoracetic acid. The solution was stirred at 40° C. for six hours, then poured into an ice-water mixture. The mixture was extracted with methylene chloride. The methylene chloride layer was washed with aqueous sodium carbonate and evaporated. A solution of sodium hydroxide (25 g) in 400 ml of methanol was added to the residue. The mixture was stirred at room temperature for 30 minutes, neutralized with 1N hydrochloric acid and extracted with methylene chloride. The methylene chloride layer was washed with aqueous sodium carbonate and water, dried with anhydrous potassium carbonate, and evaporated. The residue was vacuum distilled to give 51 g (64%) of the product.
Workup
- extractionThe mixture was extracted with methylene chloride
- washThe methylene chloride layer was washed with aqueous sodium carbonate
- customevaporated
- additionA solution of sodium hydroxide (25 g) in 400 ml of methanol was added to the residue
- stirringThe mixture was stirred at room temperature for 30 minutes
- extractionextracted with methylene chloride
- washThe methylene chloride layer was washed with aqueous sodium carbonate and water
- dry with materialdried with anhydrous potassium carbonate
- customevaporated
- distillationdistilled
Sources & evidence
- ORD record
- ord-e8dce774cf9642c88248945a8acbd9d7
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528311
Reaction notes
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