Methylparaben → HCID 22561019, compound

HRID 983649Notes

Reaction equation

HRID 983649 reaction equation
[OH:1][CH:2]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]C=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].CCOC(/N=N/C(OCC)=O)=O.O[C:44]1[CH:53]=[CH:52][C:47]([C:48]([O:50][CH3:51])=[O:49])=[CH:46][CH:45]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(OCC)C>[CH3:51][O:50][C:48]([C:47]1[CH:52]=[CH:53][C:44]([O:1][CH:2]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:25]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[CH:45][CH:46]=1)=[O:49]

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22560984HCID 22560984, compound

Product 1

HCID 22561019HCID 22561019, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Over a period of 2 h, a solution of 100.0 mg (0.24 mmol) of methyl 6-hydroxy-8-{2-[(5-phenylpentyl)oxy]phenyl}octanoate from Ex. XXXIa and 63.32 mg (0.36 mmol) of DEAD in 2.5 ml of THF was added dropwise to a solution of 55.32 mg (0.36 mmol) of methyl 4-hydroxybenzoate and 95.36 mg (0.36 mmol) of triphenylphosphine in 2.5 ml of THF. The mixture was stirred at RT for 18 h, 40 ml of diethyl ether were added, the mixture was filtered and the solvent was removed. The product was purified chromatographically (silica gel, cyclohexane/EA 10:1). This gave 63.0 mg (47.5%) of a colorless oil.

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent was removed
  3. customThe product was purified chromatographically (silica gel, cyclohexane/EA 10:1)

Sources & evidence

ORD record
ord-a034bc36a9a8470abc410725fddc59cd
Source dataset
uspto-grants-2005_03
Patent number
US06864287B1

Reaction notes

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