O-Cresol → HCID 12081207, compound

HRID 2422992Notes

Reaction equation

[C:1]12(O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3](O)([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:13]1([CH3:20])[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.P(=O)(O)(O)[OH:34].[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:19][C:18]1[CH:17]=[CH:16][C:15]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][C:3]([C:24]5[CH:25]=[CH:26][C:27]([OH:34])=[C:22]([CH3:32])[CH:23]=5)([CH2:4]4)[CH2:2]2)[CH2:8]3)=[CH:14][C:13]=1[CH3:20]

Participants

Conditions

Temperature: 90 °C

Procedure

In a flask having an inside volume of 100 mL, 8.4 g (50 mmol) of 1,3-adamantanediol, 37 g (400 mmol) of o-cresol and 3.8 g (20 mmol) of p-toluenesulfonic acid monohydrate were charged and heated to 90° C. with stirring. The mixture was heated with stirring for 10 hours until the chromatographic peak of 1,3-adamantanediol disappeared. After completion of the reaction, the reaction mixture was added with 40 mL of toluene and 0.1 g of 85% by mass phosphoric acid and, thereafter, neutralized with a 10% by mass aqueous sodium hydroxide solution. The organic layer was then washed twice with water and cooled so that crystals were precipitated. The crystals were collected by filtration, rinsed with toluene and dried to obtain 14 g (yield: 80%) of BPM13 as white solids.

Workup

customIn a flask having
temperatureThe mixture was heated
customAfter completion of the reaction
washThe organic layer was then washed twice with water
temperaturecooled so that crystals
customwere precipitated
filtrationThe crystals were collected by filtration
washrinsed with toluene
customdried
customto obtain 14 g (yield: 80%) of BPM13 as white solids

Sources & evidence

ORD record: ord-8764061a60354b76acd0fdb06e3a8575
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960483B2

Reaction notes

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