Methanol → Methyl 4-dimethylaminobenzoate

반응식

[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:18]O>>[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:18])=[O:8])=[CH:5][CH:4]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 120924-(Dimethylamino)benzoic acid

생성물 1

HCID 70994Methyl 4-dimethylaminobenzoate

실험 절차

p-Dimethylaminobenzoic acid (50 g.) and concentrated H2SO4 (25 ml.) in 350 ml. methanol were refluxed 18 hours. The reaction mixture was cooled, quenched with ice and water (350 ml.), neutralized portionwise with KHCO3 until foaming ceased, and extracted 3×200 ml. CHCl3. The organic layers were combined, washed 1×150 ml. brine, dried (MgSO4) and reduced in volume to yield crystalline title product, 52 g.; 1H-nmr: 3.02 (s, 6H), 3.87 (s, 3H), 6.66 (d, J=16 Hz, 2H), 7.95 (d, J=16 Hz, 2H).

후처리

temperatureThe reaction mixture was cooled
customquenched with ice and water (350 ml.), neutralized portionwise with KHCO3 until foaming
extractionextracted 3×200 ml
washwashed 1×150 ml
dry with materialbrine, dried (MgSO4)

출처 및 근거

ORD 기록: ord-05b040c532f649a6a9c0789244b217ae
출처 데이터셋: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04762921

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