反応 #69454

反応方程式

HCl

methyl 3-bromo-4-hydroxybenzoate

triethylamine

1-(vinyloxy)butane

→

methyl 3-acetyl-4-hydroxybenzoate

収率 82.0%

溶媒

ether

DCM

ethanol

反応条件

後処理

1. 1
   温度The reaction was cooled down
2. 2
   ろ過filtered
3. 3
   濃縮the filtrate concentrated
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGStirring
6. 6
   温度was maintained for 2 h
7. 7
   その他the organic phase was separated
8. 8
   乾燥dried over MgSO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他to afford a solid which
12. 12
    ろ過The solid was filtered off
13. 13
    濃縮the filtrate concentrated to dryness

実験手順

To a degassed solution of methyl 3-bromo-4-hydroxybenzoate (350 g, 1514.87 mmol) in ethanol (3 L) were added triethylamine (0.528 L, 3787.17 mmol), 1-(vinyloxy)butane (0.588 L, 4544.60 mmol), 1,1′-bis(diphenylphosphino)ferrocene (33.1 g, 60.6 mmol) and diacetoxypalladium (8.50 g, 37.9 mmol) under nitrogen. The mixture was heated at 70° C. overnight. The reaction was cooled down, filtered and the filtrate concentrated. The resulting solid was solubilized with DCM (2 L) and HCl 4N (1.14 L, 4544 mmol) was added under stirring. Stirring was maintained for 2 h, the organic phase was separated, dried over MgSO4, filtered and concentrated to afford a solid which was stirred in ether (5 L) for 2 h. The solid was filtered off and the filtrate concentrated to dryness to afford methyl 3-acetyl-4-hydroxybenzoate (240 g, 82%) as a beige powder. Mass spectrum: m/z [M−H]−=193.

出典