Hydrochloric Acid → Methyl 2-allyloxy-4-hydroxy-5-isopropylbenzoate

HRID 389958Notes

Reaction equation

HRID 389958 reaction equation
Cl.[CH2:2]([O:5][C:6]1[CH:15]=[C:14]([O:16]COC)[C:13]([CH:20]([CH3:22])[CH3:21])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH:3]=[CH2:4]>CO>[CH2:2]([O:5][C:6]1[CH:15]=[C:14]([OH:16])[C:13]([CH:20]([CH3:22])[CH3:21])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58236458Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate

Product 1

HCID 58236453Methyl 2-allyloxy-4-hydroxy-5-isopropylbenzoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.4 ml) was added to a solution of methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1049 mg, 3.57 mmol) in methanol (25 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the volatile material and solvent were removed in vacuo to afford methyl 2-allyloxy-4-hydroxy-5-isopropylbenzoate (880 mg, 98%) as a pale green oil. 1H NMR (DMSO-d6) 10.18 (1H, s), 7.54 (1H, s), 6.51 (1H, s), 6.03 (1H, m), 5.51 (1H, dm), 5.27 (1H, dm), 4.52 (2H, m), 3.73 (3H, s), 3.10 (1H, m), 1.15 (6H, d). MS: [M+Na]+ 273.

Workup

  1. temperatureat reflux for 3 hours
  2. customwere removed in vacuo

Sources & evidence

ORD record
ord-deb26c1cea114507b931bf986fef9361
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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