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

HRID 1586094Notes

Reaction equation

HRID 1586094 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1O)([CH3:4])([CH3:3])[CH3:2].[OH-:12].[Na+].[OH2:14].Cl.[CH:16](Cl)(Cl)Cl>>[C:1]([C:5]1[C:10]([OH:14])=[C:9]([CH:8]=[CH:7][CH:6]=1)[CH:16]=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 69232-Tert-ButylphenolHCID 14798Sodium Hydroxide3×

Product 1

HCID 36786753-tert-Butyl-2-hydroxybenzaldehydeYield 26%

Conditions

Temperature
50 °C

Procedure

A mixture of 2-tert-butylphenol (15 g, 0.010 mol), powdered NaOH (20 g,0.50 mol), H2O (3.6 ml), and CHCl3 (100 mL) was heated at 50° C. for 1 h. Then more powdered NaOH (12 g, 0.30 mol) was added at an increment of 2 g every 15 min. At the end of the NaOH additions, the reaction was continued to be heated at 56° C. for 1 h. After cooling, the reaction was acidified with HCl (12N). The chloroform fraction was separated, dried (MgSO4), and concentrated. The residue was loaded on a silica gel column eluted with CH2Cl2 to give 3-tert-butyl-2-hydroxybenzaldehyde (4.6 g, 26%) as a solid.

Workup

  1. temperatureto be heated at 56° C. for 1 h
  2. temperatureAfter cooling
  3. customThe chloroform fraction was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-6b03d569aa22421fa9ab25c43046582c
Source dataset
uspto-grants-1999_08
Patent number
US05942532

Reaction notes

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