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

HRID 2379766Notes

Reaction equation

HRID 2379766 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

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-5d4eeea35fc94eaa80790bda732e2418
Source dataset
uspto-grants-1994_11
Patent number
US05364876

Reaction notes

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