Benzoyl chloride → HCID 66891613、化合物

HRID 253290

反応式

HRID 253290 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 66891613HCID 66891613、化合物収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-15d147f08d5d4b52962ee2239796b385
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

関連ノート

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