Toluene → 4-(Benzyloxy)-2-isopropoxyphenyl benzoate

HRID 1805924Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH:24]([CH3:26])[CH3:25])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[C:27]([O:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:17][C:18]=1[O:23][CH:24]([CH3:26])[CH3:25])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (4.27 mL, 30.7 mmol) was added to a solution of 4-(benzyloxy)-2-isopropoxyphenol (2.64 g, 10.22 mmol) in dry CH2Cl2 (40.9 mL) and the resulting solution was cooled to 0° C. Benzoyl chloride (1.54 mL, 13.29 mmol) was added dropwise and the reaction was stirred at 25° C. overnight. The reaction mixture was washed with water (50 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give the crude product. This was azeoptoped with toluene to afford 4-(benzyloxy)-2-isopropoxyphenyl benzoate. LCMS calc.=385.1; found=385.0 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 8.25-8.21 (2 H, m), 7.66-7.60 (1 H, m), 7.52 (2 H, t, J=7.7 Hz), 7.47 (2 H, d, J=7.5 Hz), 7.44-7.39 (2 H, m), 7.39-7.33 (1 H, m), 7.12-7.05 (1 H, m), 6.73-6.68 (1 H, m), 6.60 (1 H, dd, J=8.7, 2.8 Hz), 5.07 (2 H, s), 4.54-4.43 (1 H, m), 1.27 (6 H, t, J=6.1 Hz).

Workup

washThe reaction mixture was washed with water (50 mL)
customThe aqueous layer was separated
extractionextracted with CH2Cl2 (2×20 mL)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated in vacuo
customto give the crude product

Sources & evidence

ORD record: ord-201dea3e07f640999ecb4b8f9a0415f2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354454B2

Reaction notes

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