Benzene → HCID 21503115, compound

HRID 1287944Notes

Reaction equation

HRID 1287944 reaction equation
Cl.[CH2:2]([O:9][CH2:10][C:11]([CH3:15])([OH:14])[CH2:12][OH:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:16]([O:21][CH2:22][CH3:23])(=[O:20])[C:17]([CH3:19])=O.C1C=CC=CC=1>O>[CH2:2]([O:9][CH2:10][C:11]1([CH3:15])[CH2:12][O:13][C:17]([CH3:19])([C:16]([O:21][CH2:22][CH3:23])=[O:20])[O:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 12041Ethyl pyruvateHCID 561596HCID 561596, compound

Product 1

HCID 21503115HCID 21503115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Dry hydrogen chloride gas was passed into a mixture of 3-benzyloxy-2-methylpropane-1,2-diol (14.9 grams) and ethyl pyruvate (9.15 grams) for 1 hour. The mixture was heated at 90° C for a further 1 hour and then cooled to 50° C. Benzene (100 milliliters) was added to the mixture and the water formed in the reaction was removed azeotropically. The cooled solution was washed with potassium carbonate solution and dried. The solvent was removed under reduced pressure and the residue was fractionally distilled to yield the desired product boiling point 124-126° C at 0.3 Torr.

Workup

  1. temperaturecooled to 50° C
  2. customwas removed azeotropically
  3. washThe cooled solution was washed with potassium carbonate solution
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. distillationthe residue was fractionally distilled

Sources & evidence

ORD record
ord-193c57e2116f41b98b2d7f0c42b1b34e
Source dataset
uspto-grants-1976_10
Patent number
US03986860

Reaction notes

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