Benzoyl chloride → HCID 66891613, 화합물

HRID 253290

반응식

HRID 253290 반응식
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[OH:1][C:2]1[C:11]([O:12][C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 75484Methyl 2,3-Dihydroxybenzoate

생성물 1

HCID 66891613HCID 66891613, 화합물수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 2,3-dihydroxybenzoate (27 g, 160 mmol) in dichloromethane (300 mL) was cooled to 0° C. and powdered potassium carbonate (23.3 g, 169 mmol) was added. The reaction mixture was then added benzoyl chloride (19.6 mL, 169 mmol) and the mixture was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned with ethyl acetate and 0.3M aqueous hydrochloric acid. The organic layer was washed with brine, dried over anhydrous magnesium sulfate. Filtration and concentration afforded 42.1 g (97%) of crude methyl 2-hydroxy-3-[(phenylcarbonyl)oxy]benzoate as an orange oil: 1H NMR (400 MHz, d4-MeOH): 8.17 (dd, J=1.6, 12.5 Hz, 2H), 7.80 (dd, J=1.6, 8.0 Hz, 1H), 7.71-7.67 (m, 1H), 7.57-7.53 (m, 2H), 7.41 (dd, J=1.8, 8.0 Hz, 1H), 6.97 (t, J=8.6 Hz, 1H), 3.96 (s, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned with ethyl acetate and 0.3M aqueous hydrochloric acid
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-15d147f08d5d4b52962ee2239796b385
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

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