Hydrochloric Acid → Phenolate Sodium

HRID 249145Notes

Reaction equation

HRID 249145 reaction equation
[C:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(Cl)(=O)C([Cl:19])=O.[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+:30].Cl>O1CCCC1.C(OCC)(=O)C>[Cl:19][C:4]([CH2:3][CH2:2][C:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])=[O:5].[C:22]1([O-:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+:30].[C:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:7])[CH2:2][CH2:3][C:4]([O:6][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 87881-(Phenylmethyl) butanedioateHCID 24758Sodium hydrideHCID 65578Oxalyl chloride

Product 3

HCID 4445035Phenolate SodiumHCID 12550027Benzyl 4-chloro-4-oxobutanoateHCID 19024784Benzyl phenyl succinate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl 3-chloroformylpropionate was prepared from benzyl hydrogen succinate (1.96 g) and oxalyl chloride (0.9 ml) in an usual manner. A solution of sodium phenolate, which was prepared from phenol (1.77 g) and sodium hydride (60% dispersion in mineral oil, 1.13 g) in tetrahydrofuran (20 ml), was added to a solution of the acid chloride in tetrahydrofuran (20 ml) at 0° C. After stirred at 0° C. for 30 minutes, the mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water, and dried over magnesium sulfate After evaporation of the solvent, the residue was chromatographed on silica gel (50 g) eluting with a mixture of ethyl acetate and hexane (1:10→1:5) to give benzyl phenyl succinate (2.15 g) as colorless crystals.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was chromatographed on silica gel (50 g)
  6. washeluting with a mixture of ethyl acetate and hexane (1:10→1:5)

Sources & evidence

ORD record
ord-d1da1bd3c7344d87b1787d545ad8dcc3
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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