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

HRID 1805925Notes

Reaction equation

[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2C=CC=CC=2)=[CH:12][C:11]=1[O:24][CH:25]([CH3:27])[CH3:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CCOC(C)=O.CCO>[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[O:24][CH:25]([CH3:27])[CH3:26])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of 10% palladium on carbon (0.543 g, 0.510 mmol) in a solution of 4-(benzyloxy)-2-isopropoxyphenyl benzoate (3.70 g, 10.21 mmol) in EtOAc (25 mL) and EtOH (5 mL) was shaken in a Parr shaker under H2 (45 psi) at 25° C. for 3 days. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 25% EtOAc in hexanes over 4536 mL) to afford 4-hydroxy-2-isopropoxyphenyl benzoate. Rf=0.28 (20% EtOAc in hexanes). LCMS calc.=295.10; found=295.07 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 8.22 (d, j=7.8 Hz, 2 H); 7.64 (t, J=7.4 Hz, 1 H); 7.51 (t, J=7.7 Hz, 2 H); 6.94 (d,J=8.6 Hz, 1 H); 6.49 (d, J=2.7 Hz, 1 H); 6.35 (dd, J=8.6, 2.7 Hz, 1 H); 4.39 (p, J=6.1 Hz, 1 H); 1.22 (d, J=6.1 Hz, 6 H).

Workup

filtrationThe reaction mixture was filtered through a plug of Celite
concentrationthe filtrate was concentrated in vacuo
customto afford the crude product
customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 25% EtOAc in hexanes over 4536 mL)

Sources & evidence

ORD record: ord-aba5d935ddc54c47811f0d33205f59e8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354454B2

Reaction notes

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