Ethyl chloroformate → HCID 58288712, compound

HRID 2382573Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]([OH:12])=[C:7]([CH3:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[C:15](=[O:16])([O:17][CH2:18][CH3:19])[O:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]([CH3:13])[C:8]=1[O:12][C:15](=[O:16])[O:17][CH2:18][CH3:19]

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 751735-tert-Butyl-3-methylpyrocatechol

Product 1

HCID 58288712HCID 58288712, compoundYield 81.4%

Procedure

Prepared from 5-tert-butyl-3-methylbenzene-1,2-diol and ethyl chloroformate; purified by flash column chromatography on silica gel to yield a sticky colorless oil (81.4%); 1H NMR (500 MHz, CDCl3, ppm) δ 7.09-7.11 (m, 2H), 4.32 (q, 2H, J=9.0 Hz), 4.31 (q, 2H, J=9.0 Hz), 2.25 (s, 3H), 1.38 (t, 3H, J=9.0 Hz), 1.37 (t, 3H, J=9.0 Hz), 1.29 (s, 9H);

Workup

custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-9ffc1f6563454ba981d6782abd9fa8f5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263520B2

Reaction notes

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