Ethylparaben → (S)-(+)-Ethyl 4-(2-methylbutyloxy)benzoate

HRID 1066546Notes

Reaction equation

[CH3:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].O[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COC(OC1C=CC(C2C=CC(C(OCCCCCCCC)=O)=CC=2)=CC=1)=O>>[CH3:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][O:4][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1

Participants

Reactant 5

HCID 8434Ethylparaben

HCID 11776Triphenylphosphine

HCID 2723602(S)-2-methyl-1-butanol

HCID 5462977Diethyl azodicarboxylate

HCID 18328376Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

Product 1

HCID 53733015(S)-(+)-Ethyl 4-(2-methylbutyloxy)benzoate

Procedure

Quantities: (S)-(-)-2-methylbutan-1-ol (5.00 g, 0.057 mol), ethyl 4-hydroxybenzoate (7) (9.47 g, 0.057 mol), DEAD (9.93 g, 0.057 mol), triphenylphosphine (14.95 g, 0.057 mol). The experimental preocedure was as described for the preparation of compound 5. The crude product was purified by column chromatography (10% petrol/dichloromethane) to give a colourless oil.

Workup

customThe crude product was purified by column chromatography (10% petrol/dichloromethane)
customto give a colourless oil

Sources & evidence

ORD record: ord-f7d370a9de3f442482bd78d5f297e004
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06242636B1

Reaction notes

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