Sodium Hydroxide → 3-Ethoxy-6-hydroxy-2-methylbenzoic acid

HRID 577549ノート

反応式

HRID 577549 の反応式
Br[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:12])[C:5]([O:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)(O)[O-:19].[Na+].CN[C@@H]1CCCC[C@H]1NC>CS(C)=O.O.S([O-])([O-])(=O)=O.[Cu+2].C(OCC)(=O)C>[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([OH:19])=[CH:3][CH:4]=1)[C:8]([OH:10])=[O:9])[CH3:15]

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86723776Methyl 6-bromo-3-ethoxy-2-methylbenzoate

生成物 1

HCID 867237773-Ethoxy-6-hydroxy-2-methylbenzoic acid収率 79%

試薬・触媒・溶媒 4

HCID 24462Copper Sulfate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

A solution of methyl 6-bromo-3-ethoxy-2-methylbenzoate (114c, 0.298 g, 1.09 mmol) in DMSO (4 mL) was treated with 10M NaOH (1.0 mL, 10 mmol) and heated at 95° C. After 1 hour, the ester was hydrolyzed. The reaction mixture was cooled to room temperature and sodium bicarbonate (0.850 g, 10.1 mmol) and water (3 mL) were added. The suspension was sonicated until homogeneous. A solution of copper(II) sulfate (0.0348 g, 0.218 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.071 mL, 0.44 mmol) in water (2.0 mL) was added. The reaction mixture was heated at 95° C. for 1 hour. The reaction mixture was cooled to room temperature, poured into ethyl acetate, and washed with 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to give 3-ethoxy-6-hydroxy-2-methylbenzoic acid (114d, 0.168 g, 79% yield) as a salmon colored solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe suspension was sonicated until homogeneous
  3. temperatureThe reaction mixture was heated at 95° C. for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with 1N HCl and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-02955aef4c42479d9c7cf881469b90a7
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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