Acetic Anhydride → HCID 3555469, compound

HRID 2377217Notes

Reaction equation

[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH:8]1([C:14]([C:16]2[CH:22]=[CH:21]C(O)=C[C:17]=2[OH:23])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[O:31]1CC[CH2:33][CH2:32]1>>[C:5]([O:4][C:1]1[CH:21]=[CH:22][C:16]([C:14]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:15])=[C:17]([O:23][C:32](=[O:31])[CH3:33])[CH:2]=1)(=[O:7])[CH3:6]

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 3673514Cyclohexyl(2,4-dihydroxyphenyl)methanone

Product 1

HCID 3555469HCID 3555469, compound

Procedure

Acetic anhydride (1.58 ml, 16.7 mmol) was added to a solution of 4-cyclohexylcarbonyl resorcinol (1.47 g, 6.68 mmol) in tetrahydrofuran (15 ml) at room temperature, followed by triethylamine (2.80 ml, 20.0 mmol) and the solution stirred for 4 h. At this time, TLC showed the clean formation of a single product (Rf 0.71) and no starting material (Rf 0.40) (Note 5). The solvent was removed under reduced pressure to give 4-cyclohexylcarbonyl resorcinol diacetate as a light-yellow oil (3.0 g) and used without further purification for the next synthetic step (Note 6).

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-4cb49b552d114a4f8a963213ba33eb93
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468464B2

Reaction notes

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