2-Methyl-3-(4-morpholinyl)benzoic acid → HCID 67112254, compound
Reaction equation
[CH3:1][C:2]1[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5]>C1COCC1>[CH3:1][C:2]1[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-methyl-3-morpholinobenzoic acid (0.5 g, 2.26 mmol) was dissolved in dry THF (12 mL) under Nitrogen and the solution was cooled at 0° C. with an ice bath. A solution of BH3 (1M in THF, 3.39 mL, 3.39 mmol) was added dropwise and the reaction was allowed to reach rt overnight. The mixture was quenched with NH4Cl (sat. solution, 2 mL) and diluted with ethyl acetate (20 mL). The organics were separated, washed with water (10 mL) and brine (10 mL) and dried over Na2SO4. The filtered solution was evaporated under vacuum to give (2-methyl-3-morpholinophenyl)methanol as a crude oil which crystallized over 2 h (0.5 g, quantitative).
Workup
- customThe mixture was quenched with NH4Cl (sat. solution, 2 mL)
- additiondiluted with ethyl acetate (20 mL)
- customThe organics were separated
- washwashed with water (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- customThe filtered solution was evaporated under vacuum
Sources & evidence
- ORD record
- ord-f047ba796cbd4cbfafe3a0c778ee1b84
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242987B2
Reaction notes
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