Hydrochloric Acid → 4-tert-Butyl-2-hydroxybenzaldehyde

HRID 1173298Notes

Reaction equation

HRID 1173298 reaction equation
Cl.N[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:5]=1[OH:14].C1N2CN3CN(C2)CN1C3.Cl.[OH:26]C(C)=O.O>O>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:3]=[O:26])=[C:5]([OH:14])[CH:6]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 98157872-Aminomethyl-5-tert-butylphenol hydrochlorideHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 137652724-tert-Butyl-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

To a solution of 1.5 g (6.9 mmol) of the product of Example 1 in 15 mL of HOAc-H2O (11:3) was added 1.17 g (8.3 mmol) of hexamethylenetetramine dissolved in 3 mL water. The reaction mixture was magnetically stirred and heated at 130° C. for 3 h at which point 13.5 mL of a 2:1 solution of conc. hydrochloric acid and water was added. The reaction mixture was heated for an additional 10 min at 130° C., then cooled to room temperature and the acetic acid was removed on a rotary evaporator. The residue was partitioned between EtOAc and water, then extracted and the organic layers were combined and dried (Na2SO4). The filtrate was passed through a layer of Celite filter aid mixed with silica gel to remove polar impurities, then evaporated. The residual oil was dried in vacuo and subsequently used in the next step without further purification.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated for an additional 10 min at 130° C.
  3. temperaturecooled to room temperature
  4. customthe acetic acid was removed on a rotary evaporator
  5. customThe residue was partitioned between EtOAc and water
  6. extractionextracted
  7. dry with materialdried (Na2SO4)
  8. filtrationfilter aid
  9. additionmixed with silica gel
  10. customto remove polar impurities
  11. customevaporated
  12. customThe residual oil was dried in vacuo
  13. customsubsequently used in the next step without further purification

Sources & evidence

ORD record
ord-93121a3d157d44a6a939e18c2b460a96
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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