Hydrochloric Acid → 3-tert-Butyl-2-hydroxybenzaldehyde

HRID 1965920Notes

Reaction equation

HRID 1965920 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C[Mg]Br.[CH2:15]=[O:16].Cl>O1CCCC1.C(OCC)C.C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:15]=[O:16])[C:6]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 69232-Tert-ButylphenolHCID 178418573HCID 178418573, compound

Product 1

HCID 36786753-tert-Butyl-2-hydroxybenzaldehydeYield 88%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To 50 mmol of 2-tert-butyl phenol in 40 ml of tetrahydrofuran was added dropwise a 3-molar methylmagnesium bromide solution (18.5 ml; 55.5 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 (100 ml), triethylamine (10 ml), and paraformaldehyde (3.75 g; 125 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-tert-butyl salicylaldehyde was purified by high vacuum distillation. Yield: 88%.

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-tert-butyl salicylaldehyde
  8. distillationwas purified by high vacuum distillation

Sources & evidence

ORD record
ord-c4e54a10c85a4be59b895e769cdce70e
Source dataset
uspto-grants-2013_04
Patent number
US08420563B2

Reaction notes

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