Lithium hydroxide, monohydrate → 4-[3-(4,4-Dimethyl-chroman-7-yl)-oct-1-enyl]-benzoic acid

HRID 899282Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH:12]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25]3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[CH3:28][C:22]1([CH3:29])[C:21]2[C:26](=[CH:27][C:18]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:11]=[CH:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=3)=[CH:19][CH:20]=2)[O:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 4-[3-(4,4-dimethyl-chroman-7-yl)-oct-1-enyl]-benzoic acid methyl ester (0.1 g, 0.25 mmole) in 25 mL of a 4:1 THF/methanol mixture was treated with a solution of 0.1 g of lithium hydroxide monohydrate in 5 mL of water. The reaction mixture was stirred at 40° C. for 2 hours, concentrated in vacuo and the pH adjusted to 3-4 with 1N HCl solution. The mixture was extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 0.06 g of 4-[3-(4,4-dimethyl-chroman-7-yl)-oct-1-enyl]-benzoic acid as a colorless glassy oil. MS (EI): (M−−1): 391.

Workup

concentrationconcentrated in vacuo
extractionThe mixture was extracted with three 25 mL portions of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-df77936bdc4246d186af34f7b31ff42d
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354931B2

Reaction notes

Loading…