3,5-Bis(tert-butyl)benzaldehyde → HCID 18705095, compound

HRID 863382Notes

Reaction equation

HRID 863382 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Mg]Cl)[CH2:18][CH3:19]>CCOCC>[C:13]([C:11]1[CH:10]=[C:7]([CH:8]([OH:9])[CH2:17][CH2:18][CH3:19])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 12682533,5-Bis(tert-butyl)benzaldehydeHCID 178455855HCID 178455855, compound

Product 1

HCID 18705095HCID 18705095, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 2.0 g (9.17 mmol) of aldehyde 18 in 10 mL of dry ether at 0 ° C. was added 5.5 mL (11.0 mmol) of propylmagnesium chloride (2.0M in ether). The reaction mixture was warmed to RT and quenched with water (50 mL), extracted (ether, 2×50 mL), washed (water then brine), dried (MgSO4), filtered and concentrated to give 2.37 g (9.05 mmol) of alcohol 19 (pure by 1H-NMR) which was directly used in the next step (98% yield): TLC (20% EtOAc-80% hexanes) Rf 0.5; 1H-NMR (CDCl3) δ0.96 (t, 3H, CH2 CH3), 1.34 (s, 18H, 6(CH3)), 1.66 (m, 2H, CH2), 1.84 (m, 1H, CH), 4.66 (m, 1H, CHOH), 7.18 (d, J=1 Hz, 2H, Ar-H), 7.34 (t, J=1 Hz, 1H, Ar-H).

Workup

  1. customquenched with water (50 mL)
  2. extractionextracted (ether, 2×50 mL)
  3. washwashed (water
  4. dry with materialbrine), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b036147c6c8c4c4ab57faac6d7cd6d79
Source dataset
uspto-grants-1998_02
Patent number
US05721103

Reaction notes

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