(Phenylmethoxy)acetaldehyde → HCID 59792597, compound

HRID 1645507Notes

Reaction equation

HRID 1645507 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:12][CH2:13][C:14]1([CH2:17]O)[CH2:16][CH2:15]1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]1[O:12][CH2:13][C:14]2([CH2:16][CH2:15]2)[CH2:17][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 108989(Phenylmethoxy)acetaldehydeHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

Product 1

HCID 59792597HCID 59792597, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of benzyloxyacetaldehyde (5 g, 33.3 mmol), 1,1-bis(hydroxymethyl)cyclopropane (4.08 g, 40 mmol), p-toluenesulfonic acid monohydrate (287 mg, 1.51 mmol) and toluene (70 ml) was refluxed for 2 hours while removing water by the Dean-Stark apparatus. After the reaction mixture was cooled to room temperature, triethylamine (4 ml) was added to the reaction mixture and the solvent was distilled off. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=5/95 to 1/9) to obtain the title compound (6.1 g, yield: 78.2%) as a light yellow oil.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customwhile removing water by the Dean-Stark apparatus
  3. additiontriethylamine (4 ml) was added to the reaction mixture
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=5/95 to 1/9)

Sources & evidence

ORD record
ord-7160f8053028449e9fc59af726c02875
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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