Carbon Dioxide → 3.5-Diethyl-4-methoxybenzoic acid

HRID 1280923ノート

反応式

HRID 1280923 の反応式
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([CH2:12][CH3:13])[CH:3]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>C1COCC1.CCOC(C)=O>[CH2:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[C:5]=1[O:10][CH3:11])[C:19]([OH:21])=[O:20])[CH3:13]

参加物

6

反応物 3

HCID 280Carbon DioxideHCID 234456364-Bromo-2,6-diethylanisoleHCID 178418339Butyllithium

生成物 1

HCID 234456633.5-Diethyl-4-methoxybenzoic acid収率 66%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

At −78° C., to a stirred solution of 4-bromo-2,6-diethylanisole (12.0 g, 49.4 mmol) in THF (329 mL) was added dropwise n-butyllithium (27.2 mL, 43.5 mmol). After 3h, the reaction was poured into crushed dry ice and allowed to warm to ambient temperature. The reaction mixture was diluted with EtOAc, concentrated, suspended in H2O, acidified (pH 1), filtered and the collected solids washed with H2O. The crude product was slurried in hexane (15 mL), collected by filtration and dried to give 6.76 g (66%) of the title compound. 1H NMR: consistent. IR (KBr) consistent. mass spectrum (EI), m/z 208 (M+). Anal. Calcd. for C12H16O3: C, 69.21; H, 7.74; N, 0.00. Found: C, 69.28; H, 7.49; N, 0.07.

後処理

  1. concentrationconcentrated
  2. filtrationfiltered
  3. washthe collected solids washed with H2O
  4. filtrationcollected by filtration
  5. customdried

出典と根拠

ORDレコード
ord-e3c8481213fe4d79a6a2015c8e1d7e4c
出典データセット
uspto-grants-2002_09
特許番号
US06451845B1

反応ノート

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