Phenylacetaldehyde → 1,4-Anhydro-6-deoxy-1,4-dimethyl-6-phenylhex-1-en-3-ulose

HRID 1605747Notes

Reaction equation

[C:1]1([CH2:7][CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][CH:11]1[C:15](=[O:16])[C:14]([OH:17])=[C:13]([CH3:18])[O:12]1.B(O)(O)O>>[OH:9][CH:8]([C:13]1([CH3:18])[C:14](=[O:17])[C:15]([OH:16])=[C:11]([CH3:10])[O:12]1)[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 998Phenylacetaldehyde

HCID 7628Boric Acid

HCID 19309Furaneol

Product 1

HCID 203733081,4-Anhydro-6-deoxy-1,4-dimethyl-6-phenylhex-1-en-3-uloseYield 23%

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6 g (0.05 mole) phenylacetaldehyde and 1.28 g (0.01 mole) of 2.5-dimethyl-4-hydroxy-3-(2H)-furanone was added 60 mg of boric acid and the mixture was stirred at 80°C for 3 hours. After working up the reaction mixture as described earlier, 0.57 g (23%) of the title compound was obtained, with melting point 157.5°-159°C.

Sources & evidence

ORD record: ord-ad0da5d9a69c4f32b691be6347281fdc
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950565

Reaction notes

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