4-(Methoxycarbonyl)-3-methylbenzoic acid → Methyl 4-(hydroxymethyl)-2-methylbenzoate

HRID 1364765Notes

Reaction equation

HRID 1364765 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[CH3:14])=[O:4]>C1COCC1>[OH:10][CH2:9][C:8]1[CH:12]=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([CH3:14])[CH:7]=1

Participants

3

Reactant 1

HCID 186730034-(Methoxycarbonyl)-3-methylbenzoic acid

Product 1

HCID 23021531Methyl 4-(hydroxymethyl)-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

410 mg of dimethyl 2-methylterephthalate was hydrolyzed via Procedure M and purified by ISCO Combi-Flash to afford 4-(methoxycarbonyl)-3-methylbenzoic acid. 255 mg of 4-(methoxycarbonyl)-3-methylbenzoic acid was cooled to 0° C. in 2 mL of THF before a solution of 2.6 mL of 1M BH3-THF complex in THF was added dropwise. The ice bath was subsequently removed and the reaction was stirred at room temperature until reaction stalled out at −50% complete by TLC. The reaction was re-cooled to 0° C. and another 2.6 mL of BH3-THF was added dropwise before the ice bath was removed. Upon completion, the reaction was re-cooled to 0° C. and quenched with 3N HCl dropwise. The aqueous layer was extracted 2 times with Ethyl Acetate and the organic layer was then extracted once with bicarbonate solution and brine, dried over Magnesium Sulfate, filtered and concentrated to give methyl 4-(hydroxymethyl)-2-methylbenzoate.

Workup

  1. additionwas added dropwise
  2. customThe ice bath was subsequently removed
  3. temperatureThe reaction was re-cooled to 0° C.
  4. additionanother 2.6 mL of BH3-THF was added dropwise before the ice bath
  5. customwas removed
  6. temperatureUpon completion, the reaction was re-cooled to 0° C.
  7. customquenched with 3N HCl dropwise
  8. extractionThe aqueous layer was extracted 2 times with Ethyl Acetate
  9. extractionthe organic layer was then extracted once with bicarbonate solution and brine
  10. dry with materialdried over Magnesium Sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-5163e39a77e84bb79875776bf364f594
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

Loading…