Hydrochloric Acid → HCID 10245237, compound

HRID 1604057Notes

Reaction equation

[CH3:1]/[C:2](/[CH:7]=[CH:8]/[CH:9]=[C:10](\[CH3:23])/[CH:11]=[CH:12]/[C:13]1[C:18]([CH3:20])([CH3:19])[C:17](=[O:21])[CH2:16][CH2:15][C:14]=1[CH3:22])=[CH:3]/[C:4]([OH:6])=[O:5].[BH4-].[Na+].Cl>C(O)C>[OH:21][CH:17]1[C:18]([CH3:20])([CH3:19])[C:13](/[CH:12]=[CH:11]/[C:10](/[CH3:23])=[CH:9]/[CH:8]=[CH:7]/[C:2](/[CH3:1])=[CH:3]\[C:4]([OH:6])=[O:5])=[C:14]([CH3:22])[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

0.5 g of (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxo-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid was dissolved in 25 ml of ethanol while warming slightly and treated with 100 mg of sodium borohydride while cooling with ice. After stirring at 0° C. for 1 hour the reaction mixture was poured on to ice-water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic phases were washed (H2O), dried (Na2SO4) and evaporated. The amorphous residue was filtered over a small column (silica gel, hexane/ethyl acetate=1:1) and recrystallized from hexane/ethyl acetate. 0.35 g of (2Z,4E,6E,8E)-9-(5-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid was obtained in yellow crystals, m.p. 152-154° C.

Workup

temperaturewhile warming slightly
temperaturewhile cooling with ice
extractionextracted with ethyl acetate
washThe organic phases were washed (H2O)
dry with materialdried (Na2SO4)
customevaporated
filtrationThe amorphous residue was filtered over a small column (silica gel, hexane/ethyl acetate=1:1)
customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-b468f057f08b496f91b41e0575c57657
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990329

Reaction notes

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