4-Hydroxybenzaldehyde → 4-Isobutoxybenzaldehyde

HRID 629136Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH:11]([CH3:13])[CH3:12].[I-].[Na+]>>[CH2:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH:11]([CH3:13])[CH3:12]

Participants

Reactant 3

HCID 1264-Hydroxybenzaldehyde

HCID 5238Sodium Iodide

HCID 65551-Bromo-2-methylpropane

Product 1

HCID 2498104-IsobutoxybenzaldehydeYield 100.6%

Procedure

The compound was synthesized as in Example 24.1, using 4-hydroxybenzaldehyde (200 mg, 1.64 mmol) and isobutyl bromide (449 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 4-isobutoxybenzaldehyde (294 mg, quant. crude) as a yellow oil that was used without further purification or characterization.

Workup

customThe compound was synthesized as in Example 24.1

Sources & evidence

ORD record: ord-e7477957f44c4f2ba7ccbb8b4cb40e2c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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