4-tert-Butylphenol → Ethyl 3-(4-benzyloxyphenyl)-2-(4-t-butylphenoxy)propionate

HRID 1860062Notes

Reaction equation

HRID 1860062 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][C:30]2[CH:31]=[CH:32][C:27]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:28][CH:29]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 73934-tert-ButylphenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Product 1

HCID 18625918Ethyl 3-(4-benzyloxyphenyl)-2-(4-t-butylphenoxy)propionateYield 41.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar manner to that described in Example 122, a reaction was carried out using ethyl 3-(4-benzyloxyphenyl)lactate (5.00 g), which is the product of Reference example 1(b), 4-t-butylphenol (2.50 g), triphenylphosphine (5.24 g) and a solution of diethylazodicarboxylate in toluene (40%, 8.80 ml) and the reaction mixture was treated to afford the desired compound (3.00 g) as a colorless oil.

Sources & evidence

ORD record
ord-e8b707fdd6b847079ec6a7634d360a89
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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