Phenol → Methyl 2-methyl-4-(phenoxymethyl)benzoate

HRID 1501003노트

반응식

HRID 1501003 반응식
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1.[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>O1CCCC1>[CH3:13][C:5]1[CH:4]=[C:3]([CH2:2][O:1][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 23021531Methyl 4-(hydroxymethyl)-2-methylbenzoate

생성물 1

HCID 89581027Methyl 2-methyl-4-(phenoxymethyl)benzoate수율 37%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of methyl 4-(hydroxymethyl)-2-methylbenzoate (126 mg, 0.7 mmol), phenol (66 mg, 0.7 mmol), triphenylphosphine (275 mg, 1.0 mmol) and tetrahydrofuran (15 mL) was stirred at room temperature for half hour. And then azodicarboxylic acid diisopropyl ester (212 mg, 1.0 mmol) was added. The mixture was stirred at room temperature for 12 hours. The resultant mixture was washed with water (20 mL×2). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give methyl 2-methyl-4-(phenoxymethyl)benzoate as a colorless oil (66 mg, 37%). 1H NMR (300 MHz, CDCl3): δ 7.92 (d, J=8.4 Hz, 1H), 7.30-7.24 (m, 4H), 6.97-6.94 (m, 3H), 5.06 (s, 2H), 3.88 (s, 3H), 2.61 (s, 3H).

후처리

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. washThe resultant mixture was washed with water (20 mL×2)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-3c594f2934f04b63bd43d6e4df45ffb4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

반응 노트

불러오는 중…