Borane;tetrahydrofuran → Methyl 4-hydroxymethyl-2-phenylbenzoate

HRID 2121148Notes

Reaction equation

HRID 2121148 reaction equation
[C:1]1([C:7]2[C:15](C)=[C:14]([C:17]([O-:19])=O)[CH:13]=[CH:12][C:8]=2[C:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.[CH2:21]1COCC1>C1COCC1>[CH3:21][O:11][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][C:14]([CH2:17][OH:19])=[CH:15][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 23436048HCID 23436048, compound

Product 1

HCID 10824066Methyl 4-hydroxymethyl-2-phenylbenzoateYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution in THF (40 mL) of 2-phenylmonomethylterephthalate (10.5 g, 41 mmol) was added borane-THF (1.0 M, 82 mL, 82 mmol) such that the reaction temperature remained below 6° C. The reaction mixture was stirred for 0.5 hours, then the cold bath was removed and stirring was continued for 2 hours. The reaction mixture was again cooled to 0° C. and aqueous HCl (3 M, 100 mL) was added slowly. The cold bath was removed and the reaction mixture was stirred for 1 hour. The THF was evaporated and the residue was extracted with ethyl acetate (3×). The combined organic extracts were washed with 1M aqueous NaOH (2×), water (2×) and brine, dried, filtered, and concentrated in vacuo to give 4-hydroxymethyl-2-phenylbenzoic acid methyl ester (9.75 g).

Workup

  1. customremained below 6° C
  2. customthe cold bath was removed
  3. stirringstirring
  4. waitwas continued for 2 hours
  5. additionaqueous HCl (3 M, 100 mL) was added slowly
  6. customThe cold bath was removed
  7. stirringthe reaction mixture was stirred for 1 hour
  8. customThe THF was evaporated
  9. extractionthe residue was extracted with ethyl acetate (3×)
  10. washThe combined organic extracts were washed with 1M aqueous NaOH (2×), water (2×) and brine
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b73879556d94fa3b92d03f0bffea5c4
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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