Hydrochloric Acid → HCID 23131710, compound

HRID 1162527Notes

Reaction equation

HRID 1162527 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].Cl>C(#N)C>[CH3:22][O:21][C:19](=[O:20])[CH2:18][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 23131710HCID 23131710, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-3-methyl-benzaldehyde 52 (0.50 g, 3.67 mmol) is dissolved in 10 mL acetonitrile. Cesium carbonate (2.07 g, 6.35 mmol) and methyl bromoacetate (0.40 mL, 4.35 mmol) are added and the suspension is vigorously stirred at room temperature overnight. The suspension is poured into 1N aqueous HCl and extracted with EtOAc. Drying over MgSO4, filtration and concentration yielded (4-formyl-2-methyl-phenoxy)-acetic acid methyl ester 53: 1H-NMR (400 MHz, CDCl3) δ=9.86 (s, 1H), 7.71 (d, J=1.6 Hz, 1H), 7.68 (dd, J=8.4, 1.6 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 4.75 (s, 2H), 3.81 (s, 3H), 2.34 (s, 3H). MS calculated for C11H13O4 (M+H+) 209.0, found 209.0.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialDrying over MgSO4, filtration and concentration

Sources & evidence

ORD record
ord-5aba0577a0c244429aaf19e0fdb23ad3
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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