2,4-Dimethylbenzoic acid → 2,4-Dimethylbenzyl alcohol

HRID 1608499

반응식

HRID 1608499 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

반응물 2

HCID 118972,4-Dimethylbenzoic acidHCID 6328200Diboron

생성물 1

HCID 278092,4-Dimethylbenzyl alcohol수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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

  1. custombefore quenching with 1N HCl and extraction of the product into ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationThe crude product was filtered through a plug of silica
  4. 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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