Hydrochloric Acid → 2-Formyl-6-phenylphenol

HRID 1965921Notes

Reaction equation

HRID 1965921 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Mg]Br.[CH2:17]=[O:18].Cl>O1CCCC1.C(OCC)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH:17]=[O:18])[C:8]=2[OH:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7017(1,1'-Biphenyl)-2-olHCID 178418573HCID 178418573, compound

Product 1

HCID 107031002-Formyl-6-phenylphenolYield 71%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To 100.6 mmol of 2-phenyl phenol in 40 ml of tetrahydrofuran was added dropwise a 3-molar methylmagnesium bromide solution (36.7 ml; 110 mmol) in diethyl ether. After two hours of stirring at room temperature, gas evolution ceased. About 90% of the solvent were removed in vacuo and toluene (250 ml), triethylamine (20 ml), and paraformaldehyde (7.55 g; 251 mmol) were added. The mixture was heated to 88° C. and held at this temperature for two hours. After cooling down to room temperature, the yellow solution was introduced into cold hydrochloric acid (1M, 250 ml). The organic phase was separated and dried over sodium sulphate. After removal of the solvent in vacuo, 3-phenyl salicylaldehyde was recrystallized from ethanol at −20° C. Yield: 71%.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated to 88° C.
  3. waitheld at this temperature for two hours
  4. temperatureAfter cooling down to room temperature
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulphate
  7. customAfter removal of the solvent in vacuo, 3-phenyl salicylaldehyde
  8. customwas recrystallized from ethanol at −20° C

Sources & evidence

ORD record
ord-be0967dcf6084174bc09df1446d83b30
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

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