2,4-Dimethylbenzoic acid → 2,4-Dimethylbenzyl alcohol
반응식
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B#B>O1CCCC1>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]참가 물질
4
실험 절차
A solution of 2,4-dimethylbenzoic acid (10 g; 66.6 mmol) in dry tetrahydrofuran (250 ml) was cooled to 0° C. and treated with a solution of diborane in tetrahydrofuran (135 ml of a 1.0M solution). The reaction mixture was stirred overnight before quenching with 1N HCl and extraction of the product into ethyl acetate. The organic phase was dried (MgSO4) and freed of solvent. The crude product was filtered through a plug of silica, eluting with 10% ethyl acetate in hexane, to obtain 8.62 g (95%) of the alcohol as a clear oil. 1H NMR (CDCl3): δ2.30, 2.32 (s, 6H total); 4.63 (d, 2H); 6.99 (m, 2H); 7.23 (d, 1H). IR (neat): 3338, 2921, 1504, 1453, 1378, 1240, 1039, 1005, 820 cm-1.
후처리
- custombefore quenching with 1N HCl and extraction of the product into ethyl acetate
- dry with materialThe organic phase was dried (MgSO4)
- filtrationThe crude product was filtered through a plug of silica
- washeluting with 10% ethyl acetate in hexane
출처 및 근거
- ORD 기록
- ord-71c795aa2f1349468b367523aa8b6110
- 출처 데이터셋
- uspto-grants-1995_03
- 특허 번호
- US05395827
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