Lithium Hydroxide → ({[5,5-Dimethyl-2-(4-methylphenyl)-1,3-dioxan-2-yl]methyl}thio)acetic acid

HRID 254093Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[CH2:7][O:6][C:5]([CH2:15][S:16][CH2:17][C:18]([O:20]CC)=[O:19])([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[O:4][CH2:3]1.[Li+].[OH-]>C1COCC1.O>[CH3:1][C:2]1([CH3:23])[CH2:7][O:6][C:5]([CH2:15][S:16][CH2:17][C:18]([OH:20])=[O:19])([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[O:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl ({[5,5-dimethyl-2-(4-methylphenyl)-1,3-dioxan-2-yl]methyl}thio)acetate (10.1 g, 29.8 mmol) was dissolved in THF (150 ml) and cooled to 0° C. LiOH (3.76 g, 89.5 mmol) in water (50 ml) was added and the mixture was stirred for two hours at room temperature. The mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with diethyl ether. The aqueous layer was acidified using 2M HCl to pH 3 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 8.7 g (94%) of the title compound as a white solid. 1H-NMR(CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.2 (s, 3H), 2.4 (s, 3H), 3.0 (s, 2H), 3.4 (s, 2H), 3.4 (s, 4H), 7.2-7.4 (m. 4H).

Workup

concentrationThe mixture was concentrated under reduced pressure
additionWater was added
extractionthe mixture was extracted with diethyl ether
extractionextracted twice with CH2Cl2
dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6e4d365405ae40339a61db82e0d8874f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07871998B2

Reaction notes

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