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Water → 4-(2,6-Dimethylphenyl)benzyl alcohol

HRID 2422241
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HRID 2422241 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C(CO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 701194-Bromobenzyl alcoholHCID 5833222,6-Dimethylphenylboronic acid

생성물 1

HCID 230828914-(2,6-Dimethylphenyl)benzyl alcohol수율 65.4%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 66808090Toluene-methanol water용매

실험 절차

(4-Bromophenyl)methanol (5.00 g, 32 mmol), (2,6-dimethylphenyl)boronic acid (5.77 g, 39 mmol) and sodium carbonate (10.2 g, 96 mmol) were dissolved in toluene-methanol-water (5:1:1, 210 mL) and, after argon substitution, tetrakistriphenylphosphinepalladium (1.85 g, 1.6 mmol) was added. The reaction mixture was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (4.44 g, yield 65%) as a white powder.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:3)

출처 및 근거

ORD 기록
ord-f0e51cde3e484437aca25064bbd1e0fb
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960369B2

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