Acetic Anhydride → 3-Acetaminobenzyl alcohol
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>O1CCCC1>[OH:9][CH2:8][C:4]1[CH:3]=[C:2]([NH:1][C:17](=[O:19])[CH3:18])[CH:7]=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (3-aminophenyl)methanol (1.87 g, 14.7 mmol) in tetrahydrofuran (10 mL) was added triethylamine (7 mL, 73.5 mmol). The reaction was cooled down to 0° C., acetic anhydride (1.5 mL, 16 mmol) was added dropwise. The reaction was warmed to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The ethyl acetate layer was dried over MgSO4, concentrated, trituated with CH2Cl2 to yield N-(3-(hydroxymethyl)phenyl)acetamide as a yellow solid (1.8 g, 74%). HPLC retention time (Method C)=1.03 min. LC/MS (ESI) (M+H)+=166.
Workup
- temperatureThe reaction was warmed to room temperature overnight
- customThe reaction mixture was partitioned between ethyl acetate and H2O
- dry with materialThe ethyl acetate layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-acf3aa17ed994537a2900057ae80fb57
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790745B2
Reaction notes
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