4-Hydroxybenzoic Acid → tert-Butyl 4-hydroxybenzoate
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[C:5]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)([CH3:9])([CH3:6])[CH3:4]Participants
3
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-Hydroxy-benzoic acid (3 g, 21.7 mmol) was stirred in toluene (35 ml, dried over mol. sieves). The solution was heated to 80° C. under N2, and N,N′-dimethylformamide di-tert-butyl acetal (10.42 mL, 43.4 mmol) was added over ca. 5 min. The mixture was stirred at 80° C. for 1 h 10 min., and cooled to rt. The solution was washed with water, twice with sat. NaHCO3 and sat. NaCl (15 mL each), dried over MgSO4, and concentrated to yield a yellow oil (2.77 g). The product was purified by flash chromatography (380 g silica, eluant: 4:6 AcOEt/heptane (2 L) and 1:1 AcOEt/heptane 700 mL) to yield white crystals (2.07 g, 49% yield).
Workup
- temperaturecooled to rt
- washThe solution was washed with water, twice with sat. NaHCO3 and sat. NaCl (15 mL each)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-21e2e35ee9b94355914bda1f5da7517b
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933021B2
Reaction notes
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