Sodium hydride → Methyl 3-methyl-4-(oxetan-3-yloxy)benzoate
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[H-].[Na+].[O:15]1[CH2:18][CH:17](O)[CH2:16]1>CN(C=O)C>[CH3:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[O:1][CH:17]1[CH2:18][O:15][CH2:16]1)[C:6]([O:8][CH3:9])=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To methyl 4-hydroxy-3-methyl-benzoate (498 mg, 3 mmol) was added DMF (3 mL) and sodium hydride (240 mg, 6.0 mmol) followed by oxetan-3-ol (445 mg, 6 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The reaction was cooled and quenched with brine solution and extracted with EtOAc (3×10 mL). The organic layer was separated and dried over sodium sulfate and evaporated to give methyl 3-methyl-4-(oxetan-3-yloxy)benzoate. To methyl 3-methyl-4-(oxetan-3-yloxy)benzoate was added sodium hydroxide (3 mL of 1 M NaOH, 3 mmol) solution and the reaction mixture was stirred for 1 hour. The reaction was acidified with 1 M HCl solution to pH 3 and extracted with EtOAc. The organics were separated and dried and concentrated in vacuo to give 3-methyl-4-(oxetan-3-yloxy)benzoic acid. ESI-MS m/z calc. 208.1. found 209.3 (M+1)+; Retention time: 1.04 minutes (3 min run).
Workup
- temperatureThe reaction was cooled
- customquenched with brine solution
- extractionextracted with EtOAc (3×10 mL)
- customThe organic layer was separated
- dry with materialdried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-94a711b0e29f4f58bec33747900d707d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181273B2
Reaction notes
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