Methanol → 6,8-Di-t-butyl-2-hydroxycarbonylchroman

HRID 988841Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=1)[O:11][CH:10]([C:19]([O:21]CCCC)=[O:20])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CO>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:14]=1)[O:11][CH:10]([C:19]([OH:21])=[O:20])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a toluene solution (183.0 g, 0.2 mol) of 6,8-di-t-butyl -2-butoxycarbonylchroman obtained in Example 2 were added 10% aqueous sodium hydroxide solution (120.0 g, 0.3 mol) and methanol (120 g), and the mixture was stirred while heating at 70° C. for 2 h. Toluene was added to the reaction mixture and the mixture was stirred and allowed to stand, and methanol and the like were removed from the aqueous layer. After the removal, aqueous sulfuric acid solution was added to the aqueous layer, and the mixture was extracted with toluene. The extract was concentrated under reduced pressure. The residue was quantitatively analyzed by liquid chromatography according to the internal standard method. As a result, 6,8-di-t-butyl-2-hydroxycarbonylchroman was obtained in a yield of 98% [net 56.92 g, 0.196 mol]. The 1H-NMR data of the obtained 6,8-di-t-butyl-2-hydroxycarbonylchroman are shown below.

Workup

stirringthe mixture was stirred
custommethanol and the like were removed from the aqueous layer
customAfter the removal, aqueous sulfuric acid solution
additionwas added to the aqueous layer
extractionthe mixture was extracted with toluene
concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record: ord-69219382d9a1492bacbedad30719a3ba
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635772B2

Reaction notes

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