Potassium Carbonate → 3-(3-Methyl-benzyloxy)-phthalic acid dimethyl ester

HRID 1915151

反応式

HRID 1915151 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 12099m-Xylyl bromideHCID 12223651Dimethyl 3-hydroxyphthalate

生成物 1

HCID 669063523-(3-Methyl-benzyloxy)-phthalic acid dimethyl ester収率 114.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.4 g, 6.4 mmol) in acetone (30 mL) and potassium carbonate (2.7 g, 19.3 mmol) was added 1-bromomethyl-3-methyl-benzene (0.91 mL, 6.7 mmol) and refluxed overnight. The solvent was evaporated and the residue was partitioned between water (100 mL) and ethyl acetate (150 mL) and washed with water (2×100 mL). The combined organic phases was dried, concentrated and purified by flash column chromatography (EtOAc/Hexane) to give 3-(3-methyl-benzyloxy)-phthalic acid dimethyl ester (2.3 g, 115% crude yield). The product was used in the next step without further purification.

後処理

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. washwashed with water (2×100 mL)
  5. customThe combined organic phases was dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (EtOAc/Hexane)

出典と根拠

ORDレコード
ord-ab46ee1344cd4e209029896b2cf227b5
出典データセット
uspto-grants-2013_12
特許番号
US08614328B2

関連ノート

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