3-(Methoxycarbonyl)benzoic acid → Benzoic acid, 3-(hydroxymethyl)-

HRID 564523Notes

Reaction equation

HRID 564523 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])=[O:4].C([BH-](CC)CC)C.[Li+]>>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([OH:4])=[O:2]

Participants

3

Reactant 2

HCID 6018803-(Methoxycarbonyl)benzoic acidHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 185629Benzoic acid, 3-(hydroxymethyl)-Yield 89.4%

Procedure

To 3-[(methyloxy)carbonyl]benzoic acid (0.18 g, 1.0 mmol) was added lithium triethyl borohydride (3.0 mL, 1.0 M in THF, 3.0 mmol) while stirring. The mixture was stirred for 3 h and then quenched with NH4Cl (sat.) and acidified with HCl (aq.). This solution was extracted with EtOAc, and the extract was dried over Na2SO4, filtered and concentrated to afford the title compound 0.136 g (89%). LC-MS m/z 153 (M+H)+.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. customquenched with NH4Cl (sat.)
  3. extractionThis solution was extracted with EtOAc
  4. dry with materialthe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5345a16779ae40a4b87de8e434c6a95b
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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