Chloromethyl Methyl Ether → Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

HRID 389956Notes

Reaction equation

HRID 389956 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24]Cl>C(#N)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:22][O:23][CH3:24])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 59167875Methyl 2,4-dihydroxy-5-(propan-2-yl)benzoate

Product 1

HCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoateYield 80.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (1.05 g, 5.0 mmol) and anhydrous potassium carbonate (828 mg, 6.0 mmol) in acetonitrile (25 ml) was treated with chloromethyl methyl ether (0.4 ml, 5.27 mmol) and the mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo and the residue treated with water (30 ml). The solid material was collected by suction filtration, rinsed with water (2×20 ml) and sucked dry under reduced pressure to afford methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1.02 g, 80%) as a colourless solid. 1H NMR (DMSO-d6) 10.61 (1H, br s), 7.58 (1H, s), 6.62 (1H, s), 5.30 (2H, s), 3.88 (3H, s), 3.42 (3H, s), 3.17 (1H, m), 1.17 (6H, d). MS: [M+H]+ 255.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with water (30 ml)
  3. filtrationThe solid material was collected by suction filtration
  4. washrinsed with water (2×20 ml)
  5. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-5957fa375e0e4b9d814f782c7db370bd
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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