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

HRID 461869

Reaction equation

HRID 461869 reaction equation
[CH:1](Cl)(Cl)Cl.[OH-:5].[Na+].[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])([CH3:10])([CH3:9])[CH3:8].Cl>O>[C:7]([C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=1[OH:17])[CH:1]=[O:5])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Chloroform (95 gm) was added dropwise with mechanical stirring to a mixture of sodium hydroxide (120 gm), water (120 gm) methanol (50 ml) and o-tert-butylphenol (100 gm) over 2 hours at 50° C. The mixture was stirred at 50° for 1 hour and then poured into water (600 ml) and acidified to pH5 with concentrated hydrochloric acid. The oily layer that formed was collected and steam distilled. The residue from the steam distillation was taken into chloroform (200 ml) and extracted with 2N sodium hydroxide. The basic extracts were acidified and the product formed was crystallised from petroleum ether to give 3-tert-butyl-4-hydroxybenzaldehyde as colourless prisms m.p. 142°.

Workup

  1. customThe oily layer that formed
  2. customwas collected
  3. distillationsteam distilled
  4. distillationThe residue from the steam distillation
  5. extractionextracted with 2N sodium hydroxide
  6. customthe product formed
  7. customwas crystallised from petroleum ether

Sources & evidence

ORD record
ord-c8778d259f4146938153f3d07f46e2c7
Source dataset
uspto-grants-1977_12
Patent number
US04064266

Linked notes

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