Hydrochloric Acid → (1R, 4R, 5S) 4-Hydroxy-6,6-dimethyl-3-oxabicyclo(3.1.0)hexan-2-one

HRID 1583831Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:25])[C@H:8]2[C@@H:4]1[C@H:5]([O:10]CC1C=CC=C(OC3C=CC=CC=3)C=1)[O:6][C:7]2=[O:9]>CC(C)=O>[CH3:2][C:3]1([CH3:25])[C@H:4]2[C@@H:8]1[C@H:7]([OH:9])[O:6][C:5]2=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

8 ml of 0.5N aqueous hydrochloric acid were slowly added to a solution of 0.805 g of the product of Example 9 melting at 82° C. in 8 ml of acetone and the mixture was stirred at 20° C. for 4 hours. The aqueous phase was extracted with petroleum ether and the aqueous phase was evaporated to dryness under reduced pressure to obtain 0.360 g of (1R,4R,5S)(-)6,6-dimethyl-4-hydroxy-3-oxabicyclo(3,1,0)hexan-2-one melting at 116° C. and having a specific rotation of [α]D20 =-114°±1.5° (c=1% in dimethylformamide).

Workup

extractionThe aqueous phase was extracted with petroleum ether
customthe aqueous phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-f441b8a56d5e4f9d9baf2c54ad04a013
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04554361

Reaction notes

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