Ethyl Acetate → HCID 12993687, compound

HRID 368937Notes

Reaction equation

[OH-].[Na+].BrBr.[C:5]([C:8]1[C:9]([Cl:23])=[C:10]2[C:15](=[C:16]([Cl:18])[CH:17]=1)[S:14](=[O:20])(=[O:19])[CH2:13][CH2:12][C:11]2([CH3:22])[CH3:21])(=[O:7])C.C(OCC)(=[O:26])C>O>[Cl:23][C:9]1[C:8]([C:5]([OH:7])=[O:26])=[CH:17][C:16]([Cl:18])=[C:15]2[C:10]=1[C:11]([CH3:22])([CH3:21])[CH2:12][CH2:13][S:14]2(=[O:20])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

1.04 Grams (26.1 mmol) of sodium hydroxide was dissolved in 20 ml of water, and 0.5 ml (8.7 mol) of bromine was added. Further, 0.93 g (2.9 mmol) of 6-acetyl-5,8-dichloro-4,4-dimethylthiochroman-1,1-dioxide was added, and the mixture was stirred for 3 hours. Then the mixture was heated at 100° C. for 5 hours. After the completion of the reaction, ethyl acetate was added, the mixture was liquid-separated, and hydrochloric acid was added to an aqueous layer to adjust the aqueous layer to a pH of 1. The extraction of the aqueous layer was carried out by adding ethyl acetate, and an organic layer was dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure to give 0.84 g (yield 90%) of 5,8-dichloro-4,4-dimethylthiochroman-6-carboxylic acid-1,1-dioxide.

Workup

additionwas added
customthe mixture was liquid-separated
additionhydrochloric acid was added to an aqueous layer
extractionThe extraction of the aqueous layer
additionby adding ethyl acetate
dry with materialan organic layer was dried over anhydrous sodium sulfate
distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record: ord-b9b59d81c72e43e4aff1940c198d9efa
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136755

Reaction notes

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