Isobutylene → HCID 21187905, compound

HRID 1940346Notes

Reaction equation

[CH3:1][C:2](=[CH2:4])[CH3:3].[OH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10].FC(F)(F)S(O)(=O)=O.C(N(CC)CC)C>ClCCl>[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10])([CH3:3])([CH3:1])[CH3:4]

Participants

Conditions

Temperature: -70 °C

Procedure

A stirred solution of isobutylene (33 mL) in dichloromethane (60 mL) at -70° C. is treated dropwise with a cooled solution of methyl 3-hydroxy-4-methoxybenzoate (6 g) in dichloromethane (60 mL), followed by trifluoromethanesulfonic acid (0.3 mL). The reaction mixture is vigorously stirred at -70° C. for 3 hours and then between -70° C. and -50° C. overnight. It is then treated with triethylamine (0.6 mL) and allowed to warm to room temperature. The resulting yellow solution is concentrated, and the residue is subjected by mplc, using diethyl ether as eluent, to give methyl 3-tert-butoxy-4-methoxybenzoate (4.93 g), m.p. 98°-100° C. [Elemental analysis: C,65.7; H,7.8%; calculated: C,65.5; H,7.6%].

Workup

custombetween -70° C. and -50° C. overnight
temperatureto warm to room temperature
concentrationThe resulting yellow solution is concentrated

Sources & evidence

ORD record: ord-ffff019974054f58bb7e18cc7a27b032
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698711

Reaction notes

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