Hydrochloric Acid → 5-Chloro-2-[(cyclohexylmethoxy)methyl]benzoic acid

HRID 493566Notes

Reaction equation

HRID 493566 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:16][C:17]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20].Cl>O1CCCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:17]([CH2:16][O:14][CH2:13][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[C:18]([CH:23]=1)[C:19]([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7507CyclohexanemethanolHCID 23665647Potassium tert-butoxideHCID 51358462Methyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 688657935-Chloro-2-[(cyclohexylmethoxy)methyl]benzoic acidYield 112.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (533 mg, 4.75 mmol) in tetrahydrofuran (10 ml) was added cyclohexylmethanol (594 mg, 5.20 mmol) in tetrahydrofuran (2.5 ml), methyl 2-(bromomethyl)-5-chlorobenzoate (250 mg, 0.95 mmol) in tetarahydrofuran (2.5 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The resulting solution was acidified with 2 N hydrochloric acid solution (pH ca. 2) at 0° C. It was extracted with dichloromethane, the organic extracts were dried over sodium sulfate and concentrated to afford 302 mg of crude 5-chloro-2-[(cyclohexylmethoxy)methyl]benzoic acid. This carboxylic acid was converted into 132 mg (31%) of the title compound according to the procedure described in step 6 of Example 1:

Workup

  1. extractionIt was extracted with dichloromethane
  2. dry with materialthe organic extracts were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7df2ef14a88747ccbb502962ddcc8c34
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

Loading…