4-Hydroxybenzaldehyde → 4-[3-(Tetrahydro-2H-pyran-2-yloxy)propoxy]benzaldehyde

HRID 440200Notes

Reaction equation

HRID 440200 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CC1C=CC(S([CH2:20][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)(=O)=O)=CC=1.ClCCl.[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>>[O:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[O:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 2723671Tetrabutylammonium HydroxideHCID 220761783-(4-Methylphenyl)sulfonyl-1-tetrahydropyranyloxypropaneHCID 23721229Sodium hydroxide methylene chloride

Product 1

HCID 224109424-[3-(Tetrahydro-2H-pyran-2-yloxy)propoxy]benzaldehyde

Procedure

In accordance with literature directions 4-hydroxybenzaldehyde is reacted with the bromo compound 2a in the presence of a phase transfer catalyst (dichloromethane/sodium hydroxide solution/tetra-n-butylammonium hydroxide). After chromatographic purification the aldehyde is obtained as a pale yellow oil.

Workup

  1. customAfter chromatographic purification the aldehyde
  2. customis obtained as a pale yellow oil

Sources & evidence

ORD record
ord-655b5f4a24d341b0b2cc29bcb4e57669
Source dataset
uspto-grants-1996_05
Patent number
US05517350

Reaction notes

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