Chloromethyl Methyl Ether → HCID 58236461, compound

HRID 389964Notes

Reaction equation

HRID 389964 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([OH:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][O:30][CH2:31]Cl>C(#N)C>[CH2:1]([O:8][C:9]1[C:18]([CH:19]([CH3:20])[CH3:21])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:22][CH2:29][O:30][CH3:31])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl Ether2×HCID 11430Potassium Carbonate2×HCID 58236452Methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate

Product 1

HCID 58236461HCID 58236461, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate (900 mg, 3.0 mmol) and anhydrous potassium carbonate (994 mg, 7.2 mmol) in acetonitrile (20 ml) was treated with chloromethyl methyl ether (0.24 ml, 6.6 mmol) and the mixture was stirred and held at 50° C. for 24 hours whereupon further anhydrous potassium carbonate (994 mg, 7.2 mmol) and chloromethyl methyl ether (0.96 ml, 26.4 mmol) were added and the mixture was stirred and held at 50° C. for a further 4 days. Upon cooling to room temperature the solvent was removed in vacuo and the residue treated with water (30 ml). The organic material was extracted with dichloromethane (2×20 ml) and the combined organic extracts were evaporated in vacuo to afford crude methyl 4-benzyloxy-5-isopropyl-2-(methoxymethyloxy)benzoate as a pale yellow oil that was used in the next step without further purification. 1H NMR (DMSO-d6) 7.57 (1H, s), 7.48 (2H, d), 7.44 (2H, t), 7.38 (1H, t), 6.90 (1H, s), 5.23 (4H, s), 3.78 (3H, s), 3.39 (3H, s), 3.21 (1H, m), 1.17 (6H, d). MS: [M+Na]+ 367.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred
  3. customwas removed in vacuo
  4. additionthe residue treated with water (30 ml)
  5. extractionThe organic material was extracted with dichloromethane (2×20 ml)
  6. customthe combined organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-9a272d2295334381aef5c1165ef9c2cc
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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