Methyl 2-(2-methylphenyl)acetate → methyl (Z)-3-hydroxy-2-(2-methylphenyl)prop-2-enoate

HRID 258165Notes

Reaction equation

HRID 258165 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].CN(C)/C=C(\C1C=CC=CC=1C)/[C:17](OC)=[O:18]>>[OH:18]/[CH:17]=[C:8](/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])\[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 7021479Methyl 2-(2-methylphenyl)acetateHCID 86747396methyl (E)-3-dimethylamino-2-(2-methylphenyl)prop-2-enoate

Product 1

HCID 13768916methyl (Z)-3-hydroxy-2-(2-methylphenyl)prop-2-enoate

Procedure

In a similar to manner to Example 1, methyl (2-methylphenyl)acetate was converted to methyl (E)-3-dimethylamino-2-(2-methylphenyl)prop-2-enoate, bp 125°-7°/0.1 mm, which on cooling gave a crystalline solid, mp 48°-49°. This was then hydrolysed in a similar manner to Example 1, but using Amberlite IR 120 resin instead of Amberlyst 15, to give methyl (Z)-3-hydroxy-2-(2-methylphenyl)prop-2-enoate, obtained as an oil and which had the following nmr spectral data: 2.15(3H,s,Me), 3.67(3H,s,CO2Me), 7.0-7.4(5H,m,ArH and =CH), 11.8(1H,d,OH)

Workup

  1. temperatureon cooling
  2. customgave a crystalline solid, mp 48°-49°

Sources & evidence

ORD record
ord-946321b8bf594b77a60ae14cb5f5c891
Source dataset
uspto-grants-1993_11
Patent number
US05264609

Reaction notes

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