Formic Acid → 4-Methyl-alpha-(4-methylphenyl)benzeneacetic acid

HRID 1269154ノート

反応式

HRID 1269154 の反応式
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:22]([OH:24])=[O:23].[OH-].[K+]>O>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:22]([OH:24])=[O:23])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 14797Potassium Hydroxide2 回HCID 2793564,4'-Dimethylbenzhydrol

生成物 1

HCID 303144-Methyl-alpha-(4-methylphenyl)benzeneacetic acid収率 26%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
15 °C

実験手順

To a 250 mL RB-flask was added 4,4′-dimethylbenzhydrol (1.06 g, 5.00 mmol) and 97% sulfuric acid (44.0 mL). The mixture was cooled to 15° C. by an ice/water bath and formic acid (12.0 mL) was added dropwise via an addition funnel over 0.5 h. The resulting foaming solution was stirred at 15° C. for 2 h. Water (300 mL) was added and the pH was adjusted to 3 with potassium hydroxide pellets and 10% KOH solution. The aqueous solution was extracted with ethyl acetate (3×100 mL) and the combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate, filtered and concentrated in vacuo to give the desired product (0.281 g, 26%) as a pale yellow solid, which was used in the subsequent step without further purification: 1H NMR (400 MHz, CD3OD) δ 7.28–6.99 (m, 8H), 6.96 (br s, 1H), 4.94 (s, 1H), 2.29 (s, 6H).

後処理

  1. extractionThe aqueous solution was extracted with ethyl acetate (3×100 mL)
  2. washthe combined organic extracts were washed with brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9ab7628de85b441d872d7c397faf11a9
出典データセット
uspto-grants-2007_04
特許番号
US07199135B2

反応ノート

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