Hydrochloric Acid → alpha-Methyl-3-nitrobenzenemethanol

HRID 231554

Reaction equation

HRID 231554 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](O)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B.CSC.Cl.C1C[O:22]CC1>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([OH:22])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 158763-Nitrophenylacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 223135alpha-Methyl-3-nitrobenzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

40 g of 3-nitrophenylacetic acid was added to a solution of 26 ml of 10M borane-methyl sulfide in 200 ml of THF, and the mixture was stirred at 25° C. for 3 hr. The solution was then acidified with HCl in methanol, followed by evaporation of the solvent. The product 3-nitrophenylethanol (IV, A=H) was partitioned between diethyl ether (Et2O) and aqueous sodium carbonate, and the Et2O layer dried over sodium sulfate. Evaporation of the Et2O afforded 34.8 g of 3-nitrophenylethanol (IV, A=H) as an oil.

Workup

  1. customfollowed by evaporation of the solvent
  2. customThe product 3-nitrophenylethanol (IV, A=H) was partitioned between diethyl ether (Et2O) and aqueous sodium carbonate
  3. dry with materialthe Et2O layer dried over sodium sulfate
  4. customEvaporation of the Et2O

Sources & evidence

ORD record
ord-070edd39b7ab4fafae69a3b8924bbd91
Source dataset
uspto-grants-1989_07
Patent number
US04847269

Linked notes

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