3-Hydroxybenzaldehyde → 3-(3-Methylbutoxy)benzaldehyde

HRID 629134Notes

Reaction equation

HRID 629134 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14].[I-].[Na+]>>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 109241-Iodo-3-methylbutane

Product 1

HCID 280656133-(3-Methylbutoxy)benzaldehydeYield 92.6%

Procedure

The compound was synthesized as in Example 24.1, using 3-hydroxybenzaldehyde (200 mg, 1.64 mmol) in place of 4-hydroxybenzaldehyde and 1-iodo-3-methylbutane (649 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 3-(isopentyloxy)benzaldehyde (292 mg, quant. crude) as a dark yellow oil that was used without further purification or characterization.

Workup

  1. customThe compound was synthesized as in Example 24.1

Sources & evidence

ORD record
ord-73e79ff375cc4d5eb4c5f7ab50471b80
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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