Phenol, 3-(1,1-dimethylethyl)- → 4-tert-Butyl-2-hydroxybenzaldehyde

HRID 2377427Notes

Reaction equation

HRID 2377427 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH:13]([O:15]C(Cl)Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:13]=[O:15])=[C:7]([OH:11])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 558102Bis(dichloromethyl) ether

Product 1

HCID 137652724-tert-Butyl-2-hydroxybenzaldehydeYield 77%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (ice bath) solution of 3-tert-butyl phenol (1.5 g, 10 mmol) in anhydrous dichloromethane was treated with titanium tetrachloride (1.86 mL, 17 mmol) followed by . . . ,-dichloromethyl ether (0.9 mL, 20 mmol). The reaction was allowed to warm to ambient temperature over 1 h, quenched cautiously with ice and water and extracted with dichloromethane. The organic extract was washed with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column_chromatography using 2-2.5% ethyl acetate in hexane as the eluent to afford the title compound (1.37 g, 77%). 1H NMR (300 MHz, CDCl3): δ 11.02(s, 1H), 9.81(s, 1H), 7.45(d, J=8.2 Hz, 1H), 7.03(dd, J=8.2, 1.7 Hz, 1H), 6.99(d, J=1.7 Hz, 1H), 1.31(s, 9H).

Workup

  1. customquenched cautiously with ice and water
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-6de02a0069b64a57bbcef612d7c4be31
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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