Hydrochloric Acid → 2-Butoxy-4-hydroxymethyl-benzoic acid methyl ester

HRID 424803ノート

反応式

HRID 424803 の反応式
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16].[Li+].[OH-:19].Cl.[Si](C=[N+]=[N-])(C)(C)C.CCCCCC>CO.O.C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:19])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 574433254-Bromomethyl-2-butoxy-benzoic acid methyl ester

生成物 1

HCID 574433312-Butoxy-4-hydroxymethyl-benzoic acid methyl ester収率 68%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of 4-bromomethyl-2-butoxy-benzoic acid methyl ester (0.0500 g, 1.67 mmol), THF (10 mL), H2O (10 mL), and LiOH (0.0160 g, 6.68 mmol) is stirred at 50° C. overnight. The mixture is acidified with 1.0 M HCl and the product is extracted with EtOAc (40 mL). The organic phase is washed with brine (20 mL) and dried (Na2SO4). After filtration, the filtrate is concentrated under reduced pressure to a residue. The residue is dissolved in CH2Cl2 (10 mL) and MeOH (10 mL) and treated with 2.0 M TMSCHN2 in hexane (5.0 mL, 10 mmol) at room temperature for 30 minutes. After concentration the residue is purified by flash chromatography to give 2-Butoxy-4-hydroxymethyl-benzoic acid methyl ester as a syrup (270 mg, 68%). LC-ES/MS: 239.3 (M+1).

後処理

  1. extractionthe product is extracted with EtOAc (40 mL)
  2. washThe organic phase is washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated under reduced pressure to a residue
  6. dissolutionThe residue is dissolved in CH2Cl2 (10 mL)
  7. concentrationAfter concentration the residue
  8. customis purified by flash chromatography

出典と根拠

ORDレコード
ord-ccd59fd8226d41239bd7395c0af33219
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

反応ノート

読み込み中…