HCID 11102070, compound → 4,6-Bis(1,1-dimethylethyl)-2,3-dihydro-2,2-dipentyl-5-benzofuranol

HRID 23811Notes

Reaction equation

C([O:4][C:5]1[C:6]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:7][C:8]2[O:12][C:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][C:9]=2[C:23]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.CC(C)([O-])C.[K+]>CCCCCCC>[C:24]([C:23]1[C:9]2[CH2:10][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[O:12][C:8]=2[CH:7]=[C:6]([C:28]([CH3:29])([CH3:31])[CH3:30])[C:5]=1[OH:4])([CH3:25])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 120 °C

Procedure

To 22 mL of heptane, 5-acetoxy-4,6-di-tert-butyl-2,2-dipentyl-2,3-dihydrobenzofuran and 1.68 g (15.0 mmol) of potassium tert-butoxide were added and the interior of the reaction vessel was argon-purged by a process consisting of depressurizing the reaction vessel and blowing it with argon. The mixture was heated on an oil bath at 120° C., refluxed for 2 hours in an argon atmosphere and cooled down to room temperature, followed by adding 30 mL of 10% hydrochloric acid dropwise. Further, the mixture was vigorously agitated for 15 minutes and then left to stand still; the organic layer was subjected to HPLC analysis and the generation of 4,6-di-tert-butyl-5-hydroxy-2,2-dipentyl-2,3-dihydrobenzofuran was confirmed by retention time (99.36% in purity).

Workup

custompurged by a process
temperaturerefluxed for 2 hours in an argon atmosphere
temperaturecooled down to room temperature
additionby adding 30 mL of 10% hydrochloric acid dropwise
waitleft

Sources & evidence

ORD record: ord-98ee55c3252e49efb5ae77ef9e695009
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852867B2

Reaction notes

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