Hydrochloric Acid → HCID 58239606, compound

HRID 1877712Notes

Reaction equation

HRID 1877712 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.C[Mg]I.O.Cl>C1(C)C(C)=CC=CC=1.C(OCC)C>[OH:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2[CH:6]=[C:7]([OH:9])[CH:8]=[C:3]([OH:2])[CH:4]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 58239601HCID 58239601, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 58239606HCID 58239606, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

17.0 g (65.2 mmol) of 2-(3′,5′-dimethoxybiphenyl-4-yl)ethanol are dissolved in 1 l of xylene, and, after addition of 110 ml (330 mmol) of a 3 M solution of methylmagnesium iodide in diethyl ether, the mixture is heated under reflux for 3 d. The batch is subsequently carefully hydrolysed by addition of water and acidified using dil. hydrochloric acid. The org. phase is separated off, washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is recrystallised from toluene, giving 4′-(2-hydroxyethyl)biphenyl-3,5-diol as a colourless solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 d
  3. customphase is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. customthe crude product is recrystallised from toluene

Sources & evidence

ORD record
ord-fe0a9c68b75e46af8771d1455539a5db
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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