Hydrochloric Acid → 4-[2-(4,4-Dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid

HRID 2415186Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][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.[OH-].[K+].C1COCC1.Cl>C(O)C.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])[CH2:11][O: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: 45 °C

Procedure

A solution of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid methyl ester (0.474 g, 1.15 mmole) in 8 mL of ethanol was treated with a solution of potassium hydroxide (1.3 g) in 5 mL of water. THF (4 mL) was added and the mixture was heated at 45° C. for two hours, diluted with 20 mL of water and the pH was adjusted to 2 with concentrated HCl. The mixture was then extracted with three 20 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow foam. The product was purified by recrystallization from acetonitrile/water to yield 0.362 g of 4-[2-(4,4-dimethyl-chroman-7-yl)-heptyloxy]-benzoic acid (1) as a white solid. M.p.: 91.5-93.3° C.

Workup

extractionThe mixture was then extracted with three 20 mL portions of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a pale yellow foam
customThe product was purified by recrystallization from acetonitrile/water

Sources & evidence

ORD record: ord-d3f9ebadae2a474789021ad2ce4d1fb1
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818652B2

Reaction notes

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