Lithium Hydroxide → {[(5,5-Dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetic acid

HRID 254082Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[CH2:7][O:6][C:5]([CH2:14][S:15][CH2:16][C:17]([O:19]CC)=[O:18])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1.[Li+].[OH-]>C1COCC1.O>[CH3:1][C:2]1([CH3:22])[CH2:7][O:6][C:5]([CH2:14][S:15][CH2:16][C:17]([OH:19])=[O:18])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl {[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}acetate (11.2 g, 34.3 mmol) was dissolved in THF (150 ml) and cooled to 0° C. LiOH (2.88 g, 68.7 mmol) in water (40 ml) was added and the mixture was stirred for 19 h. The solvents were evaporated. The crude-product was extracted between water and diethyl ether. The aqueous layer was acidified to a pH of 6 using 2M HCl and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to give 9.8 g (96%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.4 (s, 3H), 3.0 (s, 2H), 3.3 (s, 2H), 3.5 (s, 4H), 7.3-7.6 (m, 5H).

Workup

customThe solvents were evaporated
extractionThe crude-product was extracted between water and diethyl ether
extractionextracted twice with CH2Cl2
dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-431ce61b346f4972885e63027a77a394
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871998B2

Reaction notes

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