Hydrochloric Acid → HCID 21187889, compound

HRID 1584915Notes

Reaction equation

HRID 1584915 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([OH:15])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27].Cl>ClCCl>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26]([O:15][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1)=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 21187957HCID 21187957, compound

Product 1

HCID 21187889HCID 21187889, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-cyclopentyloxy-4-methoxyphenol (0.2 g) and triethylamine (1.35 mL) in dichloromethane (5 mL) is treated portionwise at 0-5° C. with 2,6-dichlorobenzoyl chloride (0.28 g), and the solution is warmed to room temperature and stirred for a further 2 hours. The reaction mixture is poured into hydrochloric acid (50 ml; 2N) and is extracted with diethyl ether (3×50 mL). The combined organic extracts are then washed with water (100 mL), and brine (100 mL), dried over magnesium sulfate and concentrated. The residual oil is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (4:1 v/v), to give (3-cyclopentyloxy-4-methoxyphenyl) 2,6-dichlorobenzoate (0.28 g), m.p. 100-101° C. [Elemental analysis: C,59.7; H,4.7%; calculated: C,59.9; H,4.8%].

Workup

  1. extractionis extracted with diethyl ether (3×50 mL)
  2. washThe combined organic extracts are then washed with water (100 mL), and brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluting with a mixture of pentane and ethyl acetate (4:1 v/v)

Sources & evidence

ORD record
ord-eb43b28d26b54c8c82b45be6c30e9591
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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