HCID 3555469, compound → HCID 69113424, compound
Reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=O)=[C:7]([O:8]C(=O)C)[CH:6]=1)(=[O:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[CH:17]1([CH2:15][C:12]2[CH:13]=[CH:14][C:5]([OH:4])=[CH:6][C:7]=2[OH:8])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A Parr hydrogenator (1 L) was charged with crude 4-cyclohexylcarbonyl resorcinol diacetate (3.0 g, 60% purity, 5.9 mmol) and acetic acid (50 ml) under nitrogen (Note 7). A suspension of 5% Pd/C (200 mg, Engelhard) in acetic acid (50 ml) was added and the reactor sealed, evacuated and purged with nitrogen (4×). The reactor was pressurized to 100 psi with hydrogen and stirred at 30° C. for 16 h, 50° C. for 16 h, recharged with catalyst (250 mg), pressurized to 200 psi H2 and stirred at 50° C. for 16 h, and finally recharged with catalyst (400 mg), pressurized to 200 psi H2 and stirred at 50° C. for 64 h (Note 8). At this time, GC showed the formation of products at the expense of starting material (Note 9). The reactor was evacuated, purged with nitrogen and the mixture filtered through celite (Note 10). The solvent was removed to give 4-cyclohexylmethyl resorcinol monoacetate as a light amber-colored oil which crystallized upon standing at room temperature (2.76 g).
Workup
- additionwas added
- customthe reactor sealed
- customevacuated
- custompurged with nitrogen (4×)
- stirringstirred at 50° C. for 16 h
- stirringstirred at 50° C. for 64 h (Note 8)
- customThe reactor was evacuated
- custompurged with nitrogen
- filtrationthe mixture filtered through celite (Note 10)
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-16f8bb39f03a4940873dc5808bcc8b1d
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468464B2
Reaction notes
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