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

HRID 1608499

Reaction equation

HRID 1608499 reaction equation
[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]

Participants

4

Reactant 2

HCID 118972,4-Dimethylbenzoic acidHCID 6328200Diboron

Product 1

HCID 278092,4-Dimethylbenzyl alcoholYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-71c795aa2f1349468b367523aa8b6110
Source dataset
uspto-grants-1995_03
Patent number
US05395827

Linked notes

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