Benzyl Alcohol → 3-Hydroxy-4-nitrobenzoic acid benzyl ester
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]Participants
7
Procedure
3-Hydroxy-4-nitro-benzoic acid 1a (10 g, 54.60 mmol) was dissolved in 125 mL of toluene followed by the addition of benzyl alcohol (9 g, 83.20 mmol) and p-toluenesulfonic acid (1 g, 5.30 mmol). The reaction solution was heated to reflux for 16 hours in water segregator. The resulting solution was added with 50 mL of ethyl acetate, washed with water (50 mL) and saturated sodium chloride solution (50 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound benzyl 3-hydroxy-4-nitro-benzoate 29a (8 g, yield: 53.7%) as a yellow solid.
Workup
- temperatureThe reaction solution was heated
- washwashed with water (50 mL) and saturated sodium chloride solution (50 mL) successively
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cd5a95e493c34e258cb36548ee36db8b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691822B2
Reaction notes
Loading…