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

HRID 1269154

반응식

HRID 1269154 반응식
[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

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 14797Potassium Hydroxide2회HCID 2793564,4'-Dimethylbenzhydrol

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
15 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ab7628de85b441d872d7c397faf11a9
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199135B2

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