1: (i) Mg, Et2O, (ii) /BRN= 741856/, benzene-1,4-diol 2: CrO3, aq. H2SO4 / diethyl ether / -20 - -15 °C 3: aq. Na2CO3 / methanol / Heating View Scheme

1: (i) Mg, Et2O, (ii) /BRN= 741856/, benzene-1,4-diol 2: CrO3, aq. H2SO4 / diethyl ether / -20 - -15 °C 3: NaOMe / methanol 4: (i) aq. NaOH, THF, (ii) aq. H2SO4 View Scheme

1: (i) Mg, Et2O, (ii) /BRN= 741856/, benzene-1,4-diol 2: CrO3, aq. H2SO4 / diethyl ether / -20 - -15 °C 3: NaOMe / methanol 4: (i) aq. NaOH, THF, (ii) aq. H2SO4 5: aq. NaOH / diethyl ether / Ambient temperature View Scheme

With  sodium nitrite in  N,N-dimethyl-formamide 7 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: 63 percent / NaNO2 / dimethylformamide / 7 h / Ambient temperature2: 74 percent / Amberlist A-21 / 16 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 63 percent / NaNO2 / dimethylformamide / 7 h / Ambient temperature2: 74 percent / Amberlist A-21 / 16 h / Ambient temperature3: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature  

Multi-step reaction with 4 steps 1: 63 percent / NaNO2 / dimethylformamide / 7 h / Ambient temperature2: 74 percent / Amberlist A-21 / 16 h / Ambient temperature3: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature4: 97 percent / methanol / 10 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 63 percent / NaNO2 / dimethylformamide / 7 h / Ambient temperature2: 74 percent / Amberlist A-21 / 16 h / Ambient temperature3: 76 percent / pyridinium chlorochromate, 3 A molecular sieves / CH2Cl2 / 24 h / Ambient temperature4: 97 percent / methanol / 10 h / Ambient temperature5: 95 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C