2-(4-Hydroxyphenyl)propionate → Methyl 2-methyl-3-(3-allyl-4-hydroxyphenyl)propionate

HRID 580979Notes

Reaction equation

HRID 580979 reaction equation
[CH3:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]CC=C)=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].O[C:19]1[CH:24]=CC(C(C)C([O-])=O)=C[CH:20]=1.C(OC1C=CC(CCC(OCC)=O)=CC=1)C=C.C(C1C=C(CCC(OCC)=O)C=CC=1O)C=C>>[CH3:1][CH:2]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[C:12]([CH2:24][CH:19]=[CH2:20])[CH:13]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 4

HCID 95433382-(4-Hydroxyphenyl)propionateHCID 19348971Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoateHCID 53880704Methyl 2-methyl-3-(4-allyloxyphenyl)propionate2×HCID 54533632Ethyl 3-[4-hydroxy-3-(prop-2-EN-1-YL)phenyl]propanoate

Product 1

HCID 54342166Methyl 2-methyl-3-(3-allyl-4-hydroxyphenyl)propionate

Procedure

Methyl 2-methyl-3-(4-allyloxyphenyl)propionate m/z 235(M+H) was prepared from methyl 2-methyl-3-(4-hydroxyphenylpropionate using the method described in Example 1 for the preparation of ethyl 3-(4-allyloxyphenyl)propionate. Methyl 2-methyl-3-(3-allyl-4-hydroxyphenyl)propionate was prepared from methyl 2-methyl-3-(4-allyloxyphenyl)propionate using the method described in Example 1 for the preparation of ethyl 3-(3-allyl-4-hydroxyphenyl)propionate. The product was isolated as an orange oil; NMR(CDCl3): 1.13(3H,d), 2.40-2.73(2H,m), 2.92(1H,q), 3.37(2H,d), 3.63(3H,s), 4.91(1H,s), 5.03-5.18(2H,m), 5.89-6.10(1H,m), 6.70(1H,m) and 6.91(2H,m); m/z 235(M+H).

Workup

  1. customThe product was isolated as an orange oil

Sources & evidence

ORD record
ord-9a35154a4fb34ed2adcd1e7f278446f1
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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