تفاعل #69454

معادلة التفاعل

HCl

methyl 3-bromo-4-hydroxybenzoate

triethylamine

1-(vinyloxy)butane

→

methyl 3-acetyl-4-hydroxybenzoate

المردود 82.0%

المذيبات

ether

DCM

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled down
2. 2
   ترشيحfiltered
3. 3
   تركيزthe filtrate concentrated
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGStirring
6. 6
   درجة الحرارةwas maintained for 2 h
7. 7
   أخرىthe organic phase was separated
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated
11. 11
    أخرىto afford a solid which
12. 12
    ترشيحThe solid was filtered off
13. 13
    تركيزthe filtrate concentrated to dryness

الإجراء التجريبي

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.

المصدر