Water → 6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarbaldehyde

HRID 2377199Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22](OC)=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:13][C:12]([CH:22]=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1 g (2.6 mmol) of methyl 6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylcarboxylate is dissolved in 40 mL of anhydrous ethyl ether, and the medium is cooled to 0° C. 130 mg (3.3 mmol) of lithium aluminum hydride are added and the reaction medium is stirred for 1 hour. The reaction is hydrolysed by sequential addition of 130 μL of water, 130 μL of 15% sodium hydroxide solution and 400 μL of water. The reaction medium is filtered and the filtrate is concentrated under reduced pressure. The residue obtained is dissolved in 30 mL of dichloromethane, and 2 g (23 mmol) of manganese dioxide are added. The medium is refluxed for 5 hours, and filtered through Celite. A yellow oil is obtained (m=780 mg; yield=85%).

Workup

filtrationThe reaction medium is filtered
concentrationthe filtrate is concentrated under reduced pressure
customThe residue obtained
temperatureThe medium is refluxed for 5 hours
filtrationfiltered through Celite
customA yellow oil is obtained (m=780 mg; yield=85%)

Sources & evidence

ORD record: ord-ade757147fc0433d88be1d0a13bf61c9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468457B2

Reaction notes

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