Benzyl 4-Hydroxybenzoate → HCID 66865525, compound

HRID 1628175Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20]([O:24][C:25](=[O:30])[C:26](Br)([CH3:28])[CH3:27])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.O>[CH2:3]([O:10][C:11](=[O:19])[C:12]1[CH:13]=[CH:14][C:15]([O:18][C:26]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:30])([CH3:28])[CH3:27])=[CH:16][CH:17]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (0.664 g, 26.28 mmol) was added to a solution of 4-hydroxy-benzoic acid benzyl ester (5.0 g, 21.90 mmol) and 2-bromo-2-methyl-propionic acid tert-butyl ester (5.86 g, 26.28 mmol) in DMF (50 mL). The resulting mixture was warmed up to 80° C. and stirred for 1 h before additional 2-bromo-2-methyl-propionic acid tert-butyl ester (5.86 g, 26.28 mmol) and sodium hydride (0.664 g, 26.28 mmol) was added. After 18 h at 80° C. about 50% product could be detected by LC-MS. The reaction mixture was diluted with water and extracted with Et2O. The combined organic layers were dried (Mg504) and evaporated and the desired product was isolated from the remaining mixture by HPLC. The title compound was obtained as an oil (2.5 g, 30.8%). 1H NMR (500 MHz, CDCl3): δ 7.96 (d, 2H), 7.43 (d, 2H), 7.37 (t, 2H), 7.33 (d, 1H), 6.82 (d, 2H), 5.32 (s, 2H), 1.60 (s, 6H), 1.40 (s, 9H).

Workup

additionwas added
extractionextracted with Et2O
dry with materialThe combined organic layers were dried (Mg504)
customevaporated

Sources & evidence

ORD record: ord-ebcdd2701c2f412092924fcff2811cc8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785681B2

Reaction notes

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