3-Hydroxybenzaldehyde → 3-(3-(Benzyloxy)propoxy)benzaldehyde

HRID 595337Notes

Reaction equation

HRID 595337 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12].CN(C)C=O.[C:21]1([CH2:27][O:28][CH2:29][CH2:30][CH2:31]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>COC(C)(C)C.O>[C:21]1([CH2:27][O:28][CH2:29][CH2:30][CH2:31][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 866376223-(3-(Benzyloxy)propoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a 3-L reaction vessel was charged and stirred cesium carbonate (209.6 g), 3-hydroxybenzaldehyde (67.6 g), dimethylformamide (DMF, 250 mL) and 3-bromopropyl phenylmethyl ether (113.4 g) at ambient temperature for ˜18 h. Water (567 mL) was added followed by tert-butyl methyl ether (907 mL). The bottom aqueous layer was separated and the organic layer washed with 1N sodium hydroxide (2×567 mL) and water (1×567 mL). The organic solution was concentrated to a minimum after which ethanol (200 proof, 907 mL) was added and the solution concentrated to a minimum and filtered though a 1-μm filter.

Workup

  1. additionwas charged
  2. customThe bottom aqueous layer was separated
  3. washthe organic layer washed with 1N sodium hydroxide (2×567 mL) and water (1×567 mL)
  4. concentrationThe organic solution was concentrated to a minimum after which ethanol (200 proof, 907 mL)
  5. additionwas added
  6. concentrationthe solution concentrated to a minimum
  7. filtrationfiltered though a 1-μm
  8. filtrationfilter

Sources & evidence

ORD record
ord-22a2ebc28da64aecafa0bb8bc1ff3990
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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