2-Bromopropane → Methyl 2-(4-isopropoxyphenyl)acetate

HRID 1852087

反応式

HRID 1852087 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

生成物 1

HCID 525538Methyl 2-(4-isopropoxyphenyl)acetate収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl 2-(4-hydroxyphenyl)acetate (10 g, 60.2 mmol), 2-bromopropane (6.49 mL, 69.2 mmol), and potassium carbonate (8.32 g, 60.2 mmol) were heated to 50° C. in DMF (100 mL) for overnight. The reaction was filtered and the organic layer was concentrated under vacuum. The crude material was purified by silica gel chromatography using a gradient of 0-20% EtOAc/hexanes. The product fractions were collected and the solvent removed under vacuum to give methyl 2-(4-isopropoxyphenyl)acetate (10 g, 80% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.22-7.14 (m, 2H), 6.88-6.82 (m, 2H), 4.53 (spt, J=6.1 Hz, 1H), 3.70 (s, 3H), 3.57 (s, 2H), 1.34 (d, J=6.0 Hz, 6H).

後処理

  1. filtrationThe reaction was filtered
  2. concentrationthe organic layer was concentrated under vacuum
  3. customThe crude material was purified by silica gel chromatography
  4. customThe product fractions were collected
  5. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-901c2da79ae248e6b47075d9e0b58102
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

関連ノート

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