Hydrochloric Acid → 3-(tert-Butyl)-4-hydroxybenzaldehyde

HRID 1505379Notes

Reaction equation

HRID 1505379 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])[CH3:3].[OH-:12].[Na+].[CH:14](Cl)(Cl)Cl.Cl>CO.O>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[OH:11])[CH:14]=[O:12])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 69232-Tert-ButylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 30176183-(tert-Butyl)-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(1,1-dimethylethyl)phenol (10 g, 66.67 mmol) was dissolved in 40 mL of MeOH and NaOH (40 g, 1 mol) dissolved in 40 mL of water was added dropwise. Then 40 mL of CHCl3 was added (during the course of 1 h) at 60° C. The reaction mixture was stirred at that temperature for 3 h. After cooling down to r.t., the mixture was cooled to 0° C. and 4M HCl was added until the solution reached pH 5-6. The mixture was extracted with DCM (three times) and the collected organic were dried over Na2SO4, filtered and evaporated. The crude was charged on a silica gel column and eluted with Cyclohexane/EtOAc (from 100:0 to 80:20 Cyclohexane/EtOAc, then plateau at 80:20) affording 766 mg of the of the title compound.

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionThe mixture was extracted with DCM (three times)
  4. dry with materialthe collected organic were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. additionThe crude was charged on a silica gel column
  8. washeluted with Cyclohexane/EtOAc (from 100:0 to 80:20 Cyclohexane/EtOAc

Sources & evidence

ORD record
ord-9d659086740e4eb9bc72cd602735cd95
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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