Lithium hydroxide, monohydrate → HCID 10137188, compound

HRID 394953Notes

Reaction equation

[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[CH:8]=2)[O:3]1.O.[OH-].[Li+]>C1COCC1.O.CCOCC>[CH3:1][C:2]1([CH3:32])[CH2:11][C:10]([CH3:12])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)[CH:8]=2)[O:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

550 mg of (RS)-methyl 4-[2-(2,2,4,4-tetramethyl-chroman-6-yl)-heptyloxy]-benzoate, dissolved in 40 ml THF/10 ml H2O/10 ml methanol, was treated with 600 mg of lithium hydroxide hydrate. The mixture was stirred at 40° C. for 6 hours. The mixture was diluted with 10 ml water and acidified to pH 2 with 1N hydrochloric. The resulting suspension was taken in 40 ml ether and the phases were separated. The aqueous phase was extracted with three portions of 20 ml ether. The combined extracts were dried over MgSO4. The solvent was removed in vacuo and the crude product was purified by trituration in acetonitrile, providing 510 mg of a pale yellow solid, m.p. 94-96° C.

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with three portions of 20 ml ether
dry with materialThe combined extracts were dried over MgSO4
customThe solvent was removed in vacuo
customthe crude product was purified by trituration in acetonitrile

Sources & evidence

ORD record: ord-c581f40e4d814b22b9291a73fd51cc84
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603012B2

Reaction notes

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