Hydrochloric Acid → 4-Formyl-3,5-dimethylbenzoic acid

HRID 1866849

反応式

HRID 1866849 の反応式
Br[C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:12].C([Li])CCC.CN([CH:21]=[O:22])C.Cl>C1COCC1>[CH:21]([C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:12])=[O:22]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 179371424-Bromo-3,5-dimethylbenzoic acidHCID 178418339Butyllithium

生成物 1

HCID 579788644-Formyl-3,5-dimethylbenzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 4-bromo-3,5-dimethylbenzoic acid (0.92 g, 4 mmol) in THF (10 mL) was cooled down to −100° C. with N2(I)-Et2O bath and added n-butyllithium (1.6 M in hexanes, 5 mL, 8 mmol) slowly. After completion of addition, the reaction mixture was warmed to −78° C. and DMF (0.74 mL, 8 mmol) was added dropwise. The resulting mixture was stirred at −78° C. for 1.5 h and allowed to warm to −20° C., followed by the addition of 2N aqueous HCl (30 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc, the combined organic phases were dried over MgSO4. The solvent was removed and the resulting residue was purified by flash column chromatography (eluent: EtOAc-hexanes-1:1) to yield 4-formyl-3,5-dimethyl-benzoic acid (10c).

後処理

  1. additionAfter completion of addition
  2. temperatureto warm to −20° C.
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialthe combined organic phases were dried over MgSO4
  6. customThe solvent was removed
  7. customthe resulting residue was purified by flash column chromatography (eluent: EtOAc-hexanes-1:1)

出典と根拠

ORDレコード
ord-a44fef9a98e04f79b395aa9be1364564
出典データセット
uspto-grants-2009_12
特許番号
US07629488B2

関連ノート

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