Water → 5-Bromo-4-methyl-2-[(phenylmethyl)oxy]benzoic acid
Reaction equation
[OH-].[Li+].O.[Br:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11]>O1CCCC1>[Br:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([CH:14]=1)[C:10]([OH:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Lithium hydroxide (0.29 g, 12.08 mmol) and water (4 ml) were added to a solution of methyl 5-bromo-4-methyl-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 8; 1.35 g, 4.03 mmol) in tetrahydrofuran (20 ml). The reaction was heated at 40° C. for 18 hours. The solvent was removed in vacuo and the residue was partitioned between water (20 ml) and ethyl acetate (30 ml). The aqueous layer was acidified to pH2 using 2N HCl. The organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a white solid. 1.26 g.
Workup
- customThe solvent was removed in vacuo
- customthe residue was partitioned between water (20 ml) and ethyl acetate (30 ml)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-b6f401c8dc134c44b577c0cbb96f00f2
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365551B2
Reaction notes
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