4-Hydroxybenzaldehyde → 4-(Tetrahydrofuran-2-ylmethoxy)benzaldehyde

HRID 629137Notes

Reaction equation

HRID 629137 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][O:13]1.[I-].[Na+]>>[O:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 14501Furan, 2-(bromomethyl)tetrahydro-

Product 1

HCID 162274124-(Tetrahydrofuran-2-ylmethoxy)benzaldehydeYield 99.9%

Procedure

The compound was synthesized as in Example 24.1, using 4-hydroxybenzaldehyde (200 mg, 1.64 mmol) and 2-(bromomethyl)tetrahydrofuran (541 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 4-((tetrahydrofuran-2-yl)methoxy)benzaldehyde (338 mg, quant. crude) as a 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-0784b84f5046440e93bb5b4c1db9d9ba
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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