Hydrochloric Acid → 4-{4-[(4-Bromobutyl)oxy]butyl}benzoic acid

HRID 1675670Notes

Reaction equation

HRID 1675670 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:13][CH:12]=1.Cl.O1CCOCC1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:23]=[CH:22][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 580247741,1-Dimethylethyl 4-{4-[(4-bromobutyl)oxy]butyl}benzoate2×

Product 1

HCID 580247764-{4-[(4-Bromobutyl)oxy]butyl}benzoic acidYield 101.6%

Procedure

1,1-Dimethylethyl 4-{4-[(4-bromobutyl)oxy]butyl}benzoate (1.05 g, 2.72 mmol, e.g. which can be as prepared in Intermediate 24) was treated with a 4M solution of HCl in 1,4-dioxane (10 ml, 40 mmol, 15 equivalents) and the mixture was allowed to stand at room temperature overnight (about 16 hours). The solvent was evaporated in vacuo followed by several co-evaporations with dichloromethane and a trituration with diethyl ether (the material failed to solidify). The diethyl ether was evaporated off to give the title compound as greenish gum (0.91 g; product contained diethyl ether by NMR). LCMS showed MH+=329/331 (Bromine isotope pattern); TRET=3.60 min.

Workup

  1. custom(about 16 hours)
  2. customThe solvent was evaporated in vacuo
  3. customThe diethyl ether was evaporated off

Sources & evidence

ORD record
ord-0c979f39e4a74e1ba04315855c3dbc0c
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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