Hydrochloric Acid → (3,5-Di-tert-butylphenyl)methanol

HRID 863381Notes

Reaction equation

HRID 863381 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[C:14]([C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=1)[CH2:8][OH:9])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 853393,5-Bis(tert-butyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12660843(3,5-Di-tert-butylphenyl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 10.0 g (42.7 mmol) of acid 1 in 20 mL of dry THF at 0° C. was added 42.7 mL (42.7 mmol) of LAH (1.0M in THF). The reaction mixture was warmed to 50° C. and stirred for 15 min. After cooling the reaction to RT, 20% aqueous HCl was added until the solution turned clear. The solution was extracted with EtOAc (2×50 mL), and the combined EtOAc extract was washed (water, then brine), dried (MgSO4), filtered and concentrated to give 8.8 g (40.0 mmol) of 17 (94% yield): The product was directly used in the next step. TLC (20% EtOAc-80% hexanes) Rf 0.4; 1H-NMR (CDCl3) δ1.33 (s, 18H, 6(CH3)), 4.68 (s, 2H, CH2) 7.22 (d, J=1 Hz, 2H, Ar-H), 7.38 (t, J=1 Hz, 1H, Ar-H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction to RT
  3. extractionThe solution was extracted with EtOAc (2×50 mL)
  4. extractionthe combined EtOAc extract
  5. washwas washed (water
  6. dry with materialbrine), dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ebf424bd2c44ea6b473d8cec183e042
Source dataset
uspto-grants-1998_02
Patent number
US05721103

Reaction notes

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