Triphenylphosphine → 3-Chloro-4-(propan-2-yloxy)benzoic acid

온도

0 °C

Propan-2-ol (2.45 ml) and PPh3 (1.18 g) were dissolved in THF (30 ml), cooled to 0° C., treated with methyl 3-chloro-4-hydroxybenzoate (6.00 g) followed by the drop-wise addition of DIAD (9.44 ml) and stirred at RT overnight. The reaction mixture was then evaporated and purified on silica cartridges (4×100 g), eluting with a 0 to 40% mixture of EtOAc in pentane to give the crude product (7.00 g) as a colourless oil. This was dissolved in MeOH (30 ml) and 2 M aqueous NaOH (30 ml) and stirred at RT for a weekend. The reaction mixture was then evaporated and re-dissolved in H2O. This solution was washed with Et2O, acidified to pH=1 and extracted with Et2O. These latter extracts were dried over MgSO4, filtered and evaporated to give the title compound (4.16 g) as a white solid. δH (MeOD, 400 MHz): 1.37 (6H, d), 4.77 (1H, septet), 7.12 (1H, d), 7.90 (1H, d), 7.98 (1H, s). MS (ES): C10H11ClO3 requires 214; found 215 (MH+).

1. customThe reaction mixture was then evaporated
2. custompurified on silica cartridges (4×100 g)
3. washeluting with a 0 to 40% mixture of EtOAc in pentane
4. customto give the crude product (7.00 g) as a colourless oil
5. customThe reaction mixture was then evaporated
6. dissolutionre-dissolved in H2O
7. washThis solution was washed with Et2O
8. extractionextracted with Et2O
9. dry with materialThese latter extracts were dried over MgSO4
10. filtrationfiltered
11. customevaporated

ORD 기록

ord-5d4f0fa8162f474ab7b4d837b2dc3c1c

출처 데이터셋

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08101775B2