Isobutylene → HCID 21187905, compound

HRID 356964Notes

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 mpic, 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-b3bcad4ba3994741bae6aada7c8b7b36
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840724

Reaction notes

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