Hydrochloric Acid → 4-(3-Benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde

HRID 1798152Notes

Reaction equation

HRID 1798152 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:16]([CH:17]=[O:18])=[C:15]([O:22]COC)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[O:12][C:13]1[CH:20]=[C:19]([CH3:21])[C:16]([CH:17]=[O:18])=[C:15]([OH:22])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866539784-(3-Benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde

Product 1

HCID 866539794-(3-Benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-benzyloxy-phenoxy)-2-methoxymethoxy-6-methyl-benzaldehyde (3.3 g, 8.8 mmol) in THF (50 mL) was added 6M HCl (6 mL) and the solution refluxed for 2 hours. The volatile organics were removed in vacuo and the aqueous residue extracted with EtOAc (2×25 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (hex:EtOAc 70:30) to give 4-(3-benzyloxy-phenoxy)-2-hydroxy-6-methyl-benzaldehyde (2.5 g, 85%). 1H NMR (400 MHz, CDCl3): δ 10.13 (s, 1H), 7.43-7.25 (m, 6H), 6.85 (d, J=8.4 Hz, 1H), 6.68 (d, J=13.2 Hz, 2H), 6.34 (s, 1H), 6.24 (s, 1H), 5.04 (s, 2H), 2.52 (s, 3H). MS (ESI) m/z=335 [M+H]+.

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. customThe volatile organics were removed in vacuo
  3. extractionthe aqueous residue extracted with EtOAc (2×25 mL)
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash column chromatography (hex:EtOAc 70:30)

Sources & evidence

ORD record
ord-cabb06ac18e74e9f92b75006de0c1427
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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