Hydrochloric Acid → 4-Formyl-2-pentyl-benzoic acid methyl ester

HRID 2261805Notes

Reaction equation

HRID 2261805 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2OCC=C[O:11]2)=[CH:6][C:5]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 675283664-[1,3]Dioxin-2-yl-2-pentyl-benzoic acid methyl ester

Product 1

HCID 574433334-Formyl-2-pentyl-benzoic acid methyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1,3]Dioxin-2-yl-2-pentyl-benzoic acid methyl ester (360 mg, 1.3 mmol) in THF (5.0 mL) is added concentrated HCl (0.55 mL, 6.5 mmol). The reaction is stirred for 2.0 h. The reaction mixture is partitioned between EtOAc (20 mL) and water (20 mL). The organic phase is washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as syrup (236 mg, 98%). LC-ES/MS m/e 235.3 (M+1).

Workup

  1. customThe reaction mixture is partitioned between EtOAc (20 mL) and water (20 mL)
  2. washThe organic phase is washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-b6cc4ca4ce1f4a4592f6788590ebba7c
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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