Hydrochloric Acid → 5-tert-Butyl-4-hydroxy-2-methylbenzaldehyde

HRID 23466

Reaction equation

HRID 23466 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[OH:16])([CH3:8])([CH3:7])[CH3:6].[CH:17](OCC)(OCC)[O:18]CC.Cl>ClC1C=CC=CC=1>[C:5]([C:9]1[C:10]([OH:16])=[CH:11][C:12]([CH3:15])=[C:13]([CH:14]=1)[CH:17]=[O:18])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69376-tert-Butyl-m-cresolHCID 31214Ethyl orthoformateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 112869885-tert-Butyl-4-hydroxy-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
-10 °C

Procedure

Aluminum chloride (26.6 g, 200 mmol) was added to chlorobenzene (40 mL), and the mixture was cooled to −10° C. A solution of 2-tert-butyl-5-methylphenol (16.4 g, 100 mmol) in triethyl orthoformate (32.5 g, 220 mmol) was added dropwise. When addition was complete, the reaction mixture was warmed to 0° C. to 5° C. and kept at that temperature for 6 hours. Five percent HCl (100 mL) was added, and the mixture was extracted with 1:1 EtOAC:toluene. The organic phase was extracted with 23% KOH (3×50 mL) and water (25 mL), and the water extract was combined with the KOH extracts. The pH of the combined aqueous extracts was adjusted to 4 with 37% HCl. The resulting precipitate was filtered, washed with water (3×50 mL), and dried to give the title compound, mp 171-171° C.

Workup

  1. additionWhen addition
  2. temperaturethe reaction mixture was warmed to 0° C. to 5° C.
  3. extractionthe mixture was extracted with 1:1 EtOAC
  4. extractionThe organic phase was extracted with 23% KOH (3×50 mL) and water (25 mL)
  5. extractionthe water extract
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water (3×50 mL)
  8. customdried

Sources & evidence

ORD record
ord-d2ac3b7a52c4435a87fc980e037e3c53
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Linked notes

Loading…