Hydrochloric Acid → Methyl 5-(hydroxymethyl)-2-methoxybenzoate

HRID 323406

반응식

HRID 323406 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].O1CCCC1.O1CCCC1.B.Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuran2회HCID 10856352Methyl 5-formyl-2-methoxybenzoate

생성물 1

HCID 18465013Methyl 5-(hydroxymethyl)-2-methoxybenzoate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Combine methyl 2-methoxy-5-formylbenzoate (0.1 g, 0.5 mmol) and tetrahydrofuran (2 mL). Cool in an ice bath. Add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 1.5 hours, again add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 2 hours, add a 1 M aqueous solution of hydrochloric acid (2 mL) and stir. After 15 minutes, dilute the reaction mixture with ethyl acetate. Separate the layers, extract the aqueous layer three times with ethyl acetate and combine the organic layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-hydroxymethylbenzoate: Rf=0.32 (silica gel, ethyl acetate).

후처리

  1. temperatureCool in an ice bath
  2. waitAfter 2 hours
  3. waitAfter 15 minutes
  4. customSeparate the layers
  5. extractionextract the aqueous layer three times with ethyl acetate
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-42a1c33b2e044642aa67700e7383a44c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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