4-Chloro-3-methoxybenzoic acid → (4-Chloro-3-methoxyphenyl)methanol

HRID 562684Notes

Reaction equation

HRID 562684 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 20633784-Chloro-3-methoxybenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 10910038(4-Chloro-3-methoxyphenyl)methanolYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-methoxybenzoic acid (4.88 g, 26.2 mmol) in THF (50 mL) was added borane-THF complex (52 mL 1M solution in THF, 52 mmol) via addition funnel over 10 min. The reaction mixture was refluxed for 2 hr, cooled, extracted with EtOAc, washed with water, 5% Na2CO3 and brine, dried and concentrated in vacuo to give (4-chloro-3-methoxyphenyl)methan-1-ol (4.5 g, 99%). ES-MS (M+H−H2O)+=155, 157 (Cl).

Workup

  1. additionvia addition funnel over 10 min
  2. temperatureThe reaction mixture was refluxed for 2 hr
  3. temperaturecooled
  4. extractionextracted with EtOAc
  5. washwashed with water, 5% Na2CO3 and brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c262f28a375b4b27b75682ab1f478255
Source dataset
uspto-grants-2011_11
Patent number
US08067428B2

Reaction notes

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