Hydrochloric Acid → 3-Iodo-4-methoxybenzoic acid

HRID 1511209ノート

反応式

HRID 1511209 の反応式
[OH-].[Li+].[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([O:9]C)=[O:8].Cl>C1COCC1.CO.O.O>[I:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([OH:9])=[O:8]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 316980Methyl 3-iodo-4-methoxybenzoate

生成物 1

HCID 6241583-Iodo-4-methoxybenzoic acid収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

Lithium hydroxide (72 mg, 1.71 mmol) was added to a mixture of methyl 3-iodo-4-methoxybenzoate (100 mg, 0.342 mmol) in 3.0 mL of a 3:1:1 THF-MeOH-water solution at room temperature. The mixture was stirred for 8 hours in the dark and than diluted with H2O (2 mL). The solution was acidified to pH=2 by the dropwise addition of concentrated HCl. The solution was extracted twice with EtOAc (10 mL portions) and the combined organic layers dried (Na2SO4), filtered, and concentrated to afford acid 26 (95 mg, 100%) as a yellow solid that was suitable for use without further purification: 1H NMR (400 MHz, DMSO) δ 8.24 (d, J=2.0 Hz, 1H), 7.92 (dd, J=2.0, 8.7 Hz, 1H), 7.07 (d, J=8.7 Hz, 1H), 3.88 (s, 3H).

後処理

  1. extractionThe solution was extracted twice with EtOAc (10 mL portions)
  2. dry with materialthe combined organic layers dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-2fba7226408948948a045a6e73098efd
出典データセット
uspto-grants-2012_07
特許番号
US08212011B2

反応ノート

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