Benzyl Bromide → Dimethyl 5-bentyloxy-isophthalate

HRID 852543ノート

反応式

HRID 852543 の反応式
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][O:16][C:17](=[O:29])[C:18]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[CH:19]=1>CC(C)=O>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[C:26]([O:28][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:27]=[C:18]([C:17]([O:16][CH3:15])=[O:29])[CH:19]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

生成物 1

HCID 7643390Dimethyl 5-bentyloxy-isophthalate収率 105.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

K2CO3 (21 g, 153 mmol, 2 equiv) and benzyl bromide (11 ml, 92 mmol, 1.2 equiv) were added to a solution of 5-hydroxy-isophthalic acid dimethyl ester (D42) (16.1 g, 76.7 mmol, 1 equiv) in acetone (400 ml) at room temperature. The resulting solution was refluxed for 18 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between H2O and AcOEt. The aqueous phase was extracted with AcOEt and the combined organic layers were washed with 2N aqueous NaOH solution and brine, dried over MgSO4 and concentrated in vacuo to give 5-benzyloxy-isophthalic acid dimethyl ester (D44) (24.2 g, 105%) as a white solid. [M+H]+=301.0, RT=3.50 min

後処理

  1. temperatureThe resulting solution was refluxed for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between H2O and AcOEt
  4. extractionThe aqueous phase was extracted with AcOEt
  5. washthe combined organic layers were washed with 2N aqueous NaOH solution and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-71d980f29f114cd18960011bb8d0f879
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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