Methylparaben → 4-Phenethyloxybenzoic Acid Methyl Ester

HRID 970786노트

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HRID 970786 반응식
[H-].[Na+].C1COCC1.[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O.CN(C)C=O>[CH3:8][O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 7456MethylparabenHCID 7666Phenethyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

생성물 1

HCID 120638344-Phenethyloxybenzoic Acid Methyl Ester수율 29.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

NaH (60%) (4.400 g, 120.0 mmol) was added to freshly distilled THF chilled to 0° C., followed by 4-hydroxybenzoic acid methyl ester 9 (15.215 g, 100.0 mmol). After H2 evolution ceased, dimethylformamide (DMF) (20 ml) was added clearing the cloudy solution followed by phenethyl bromide 8 (16.39 ml, 120.0 mmol), and the mixture was stirred at 80° C. for 24 hours. Upon cooling, the mixture was poured into H2O and extracted. The organic extracts were combined, washed, dried, and evaporated. The residue was purified by chromatography to give about 7.6 g of 4-phenethyloxybenzoic acid methyl ester 10.

후처리

  1. temperatureUpon cooling
  2. extractionextracted
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-95b31d6f44ce49f48e31e078970f5722
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312230B2

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