Hydrochloric Acid → HCID 11776502, compound

HRID 1108608Notes

Reaction equation

HRID 1108608 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1)=[O:4].CCOCC.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCCC1>[OH:12][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 15294Methyl 4-FormylbenzoateHCID 178418255HCID 178418255, compound

Product 1

HCID 11776502HCID 11776502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25.2 g (154 mmol) of methyl terephthalaldehydate was dissolved in 200 ml of tetrahydrofuran. 51.2 ml(154 mmol) of a 2M ether solution of phenyl magnesium bromide was added dropwise thereto under cooling in a sodium chloride-ice bath with stirring for 12 minutes and the mixture was stirred for further 20 minutes. Dilute hydrochloric acid was added to the resulting reaction mixture, then the obtained mixture was extracted twice with ethyl acetate. After the organic phase was washed with brine and dried (MgSO4), the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1 (v/v)) to obtain 31.7 g (131 mmol) of methyl α-hydroxy-α-phenyl-p-toluate as a pale yellow oily substance. Its spectroscopic data are as follows:

Workup

  1. temperatureunder cooling in a sodium chloride-ice bath
  2. stirringthe mixture was stirred for further 20 minutes
  3. extractionthe obtained mixture was extracted twice with ethyl acetate
  4. washAfter the organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1 (v/v))

Sources & evidence

ORD record
ord-cca66aab19d140479e0cb739411960af
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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