Sulfuric Acid → (Phenylmethoxy)acetaldehyde

HRID 54762Notes

Reaction equation

HRID 54762 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.S(=O)(=O)(O)O>O1CCCC1>[C:8]1([CH2:7][O:6][CH2:5][CH:4]=[O:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 4321487Benzyloxyacetaldehyde diethyl acetal

Product 1

HCID 108989(Phenylmethoxy)acetaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirring mixture of 100 g of benzyloxyacetaldehyde diethyl acetal, 500 ml of tetrahydrofuran and 400 ml of 2N sulfuric acid is heated at reflux temperature for 45 minutes. The resulting solution is cooled to room temperature, concentrated in vacuo to 400 ml volume and diluted with 1000 ml of chloroform. The organic layer is washed with water, cold saturated sodium bicarbonate, saturated sodium chloride and dried. The filtrate is evaporated in vacuo to give the product as an oil. The crude oil is purified by Kugelrohr distillation (bath temperature 100° C.) to give 59.0 g of the desired product as a colorless oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 45 minutes
  3. concentrationconcentrated in vacuo to 400 ml volume
  4. additiondiluted with 1000 ml of chloroform
  5. washThe organic layer is washed with water, cold saturated sodium bicarbonate, saturated sodium chloride
  6. customdried
  7. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-8e461e93620b4b0abc37d28ccd6491b7
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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