Hydrochloric Acid → 6-Benzyloxy-2-bromo-naphthalen-1-ol

HRID 1513862Notes

Reaction equation

HRID 1513862 reaction equation
C[O-].[Na+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[C:17](Br)([Br:23])[CH2:16][CH2:15]2)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.O>CO>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([OH:22])=[C:17]([Br:23])[CH:16]=[CH:15]2)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 670047946-(Benzyloxy)-2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 670051586-Benzyloxy-2-bromo-naphthalen-1-olYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Add 1M sodium methoxide (215 mL, 0.99 mol) into a solution of 6-benzyloxy-2,2-dibromo-3,4-dihydro-2H-naphthalen-1-one (205 g, 0.5 mol) in methanol (1.3 L). Heat the suspension to dissolution. Cool the reaction mixture to 0° C. and add 1N HCl (540 mL). Add H2O (3 L) and cool to 3° C. to obtain a solid. Filter and dry the solid to obtain 152 g (92%) of 6-benzyloxy-2-bromo-naphthalen-1-ol.

Workup

  1. temperatureHeat the suspension
  2. dissolutionto dissolution
  3. customto obtain a solid
  4. filtrationFilter
  5. customdry the solid

Sources & evidence

ORD record
ord-794f2739d0b64b4282f2d9eaf80dae75
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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