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

HRID 424803노트

반응식

HRID 424803 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 574433312-Butoxy-4-hydroxymethyl-benzoic acid methyl ester수율 68%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ccd59fd8226d41239bd7395c0af33219
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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