Hydrochloric Acid → HCID 10136425, compound

HRID 899279Notes

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][S: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)[S:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 4-[2-(4,4-dimethyl-thiochroman-7-yl)-heptyloxy]-benzoic acid methyl ester (0.715 g, 1.68 mmole) in 12 mL of ethanol was treated with a solution of potassium hydroxide (1.9 g) in 7.5 mL of water. THF (5 mL) was added and the mixture was heated at 45° C. for two hours, diluted with 30 mL of water and the pH adjusted to 2.0 with concentrated HCl. The mixture was extracted with three portions of 30 mL of ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow foam. The product was purified by trituration in pentane, to yield 0.617 g of 4-[2-(4,4-dimethyl-thiochroman-7-yl)-heptyloxy]-benzoic acid as an off-white solid. M.p.: 123.0-123.5° C.

Workup

extractionThe mixture was extracted with three portions of 30 mL of ethyl acetate
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a pale yellow foam
customThe product was purified by trituration in pentane

Sources & evidence

ORD record: ord-949e79ee09074da59496a0d145f470bb
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354931B2

Reaction notes

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