Ethyl Acetate → 5-(9-Methoxycarbonyl-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

HRID 1022416Notes

Reaction equation

[C:1]([O:5][C:6](=[O:21])[C:7]1[CH2:8][C:9](O)([CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:23].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39].CCOC(C)=O>CC(C)=O.O>[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:19]=[C:18]([O:23][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

3-Hydroxy-isophthalic acid di-tert-butyl ester (90 mg, 0.3 mmol) was dissolved in dry acetone (5 ml), K2CO3 (90 mg, 0.65 mmol) and methyl 10-bromodecanoate (0.075 ml, 0.3 mmol) was added. The mixture was heated to reflux. The heating caused dissolution of the K2CO3. After a while, a precipitate was formed. Reflux (50° C.) was continued over night. More K2CO3 (30 mg, 0.2 mmol) and methyl 10-bromodecanoate (0.025 ml, 0.1 mmol) was added. The mixture was refluxed at 50° C. over night. To the dry reaction mixture EtOAc and water was added. After extraction, the organic layer was washed with water and brine, dried (Na2SO4) and concentrated to give the crude title compound as a clear oil.

Workup

temperatureThe mixture was heated to reflux
customAfter a while, a precipitate was formed
waitwas continued over night
temperatureThe mixture was refluxed at 50° C. over night
additionwas added
extractionAfter extraction
washthe organic layer was washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-8fa3a90c8c5245e097778c80c620e377
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722620B2

Reaction notes

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