Benzyl Bromide → 2-(Benzyloxy)-3-(tert-butyl)benzaldehyde

HRID 41338Notes

Reaction equation

HRID 41338 reaction equation
[C:1]([C:5]1[C:6]([OH:13])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:14]([O:13][C:6]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 115435672-(Benzyloxy)-3-(tert-butyl)benzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-tert-butyl-2-hydroxybenzaldehyde (11.3 g, 63.5 mmol, 1.0 equiv), benzyl bromide (10.8 g, 7.5 mL, 63.5 mmol, 1.0 equiv), powdered K2CO3 (17.5 g, 127 mmol, 2.0 equiv) and MeCN (300 mL) was refluxed for 4 hr. The pale green suspension was cooled to room temperature, filtered, washing the solids with EtOAc (150 mL). The filtrate was concentrated under reduced pressure to give a pale green oil. The crude product was chromatographed on silica gel (175 g) packed in heptanes (loaded as a solution in heptanes). The column was eluted with heptanes (1 L), 2% MTBE/heptanes (1 L) and 3% MTBE/heptanes (1.5 L). Product fractions were concentrated under reduced pressure to give 14.6 g (86%) of 21 as a yellow oil.

Workup

  1. temperaturewas refluxed for 4 hr
  2. filtrationfiltered
  3. washwashing the solids with EtOAc (150 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a pale green oil
  6. customThe crude product was chromatographed on silica gel (175 g)
  7. washThe column was eluted with heptanes (1 L), 2% MTBE/heptanes (1 L) and 3% MTBE/heptanes (1.5 L)
  8. concentrationProduct fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-311c046570084434ab178d80369b9607
Source dataset
uspto-grants-2013_09
Patent number
US08530593B2

Reaction notes

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