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

HRID 323406

反応式

HRID 323406 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuran2 回HCID 10856352Methyl 5-formyl-2-methoxybenzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-42a1c33b2e044642aa67700e7383a44c
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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