Hydrochloric Acid → 4-(1-Formyl-heptyl)-benzoic acid methyl ester

HRID 658306Notes

Reaction equation

HRID 658306 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[CH:17][O:18]C)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:17]=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 684911714-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester

Product 1

HCID 866258334-(1-Formyl-heptyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester (3.5 g, 12.68 mmol) is dissolved in tetrahydrofuran (50 mL) and concentrated hydrochloric acid (5 mL) is added. The system is purged of air with nitrogen and heated to reflux for 6 h. The reaction is monitored by HPLC. The reaction is allowed to cool to room temperature and then neutralized with 30% potassium hydroxide solution and bicarbonate. The two phases are separated and the aqueous extracted a second time with diethyl ether. The combined organic extracts are washed with brine, dried over sodium sulfate, and concentrated. The crude material is loaded onto a silica gel column and purified using hexanes/ethyl acetate. MS (ES): 261.2 [M+H]−.

Workup

  1. customThe system is purged of air with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 6 h
  4. customThe two phases are separated
  5. extractionthe aqueous extracted a second time with diethyl ether
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-eebea886a7004a2e99d91c2deec1147c
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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