Methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate → 3-Chloro-4,5-bis(cyclopentyloxy)benzoic acid

HRID 62731Notes

Reaction equation

HRID 62731 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:18][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:11]=1[O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([O:7]C)=[O:6]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[C:11]=1[O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1)[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 67041558Methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate

Product 1

HCID 670417523-Chloro-4,5-bis(cyclopentyloxy)benzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Chloro-4,5-bis(cyclopentyloxy)benzoic acid (5) (380 mg, 99%) was prepared from methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate (4) (400 mg, 1.18 mmol) using a procedure essentially the same as in Step (ii) for AAA-001, except that 1,4-dioxane (10 mL) was used instead of THF: m/z 323 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 13.07 (1H, br s), 7.52 (1H, d), 7.45 (1H, d), 4.97-4.91 (2H, m), 1.99-1.90 (2H, m), 1.70-1.57 (14H, m).

Sources & evidence

ORD record
ord-bc56ca8647424c439b0877a6aceb0b33
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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