3-Cyclohexene-1-carboxylic acid → HCID 10352816, compound

HRID 1034201Notes

Reaction equation

HRID 1034201 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1>C(OCC)(=O)C>[C:1]1([C:3]2[CH2:2][C@H:1]([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH:4]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 209033-Cyclohexene-1-carboxylic acid

Product 1

HCID 10352816HCID 10352816, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Phenyl-3-cyclohexenecarboxylic acid (8.1 g, Step C) is dissolved in 2-butanone (20 mL) and (S)-α-methylbenzylamine (4.85 g) in 2-butanone (10 mL) added. The salt precipitates and more 2-butanone (200 mL) is added and the mixture heated to dissolve the salt. The salt recrystallizes on cooling to 25° C. and it is collected and dried to give 10.02 g of the salt. The salt is recrystallized 5 times from 2-butanone to give 3.14 g of a white powder. The powder is slurried in ethyl acetate and washed with 2N hydrochloric acid. The ethyl acetate layer is dried over magnesium sulfate, filtered, and evaporated to give (R)-3-phenyl. 3-cyclohexenecarboxylic acid as a white powder; mp 77°-80° C.

Workup

  1. washwashed with 2N hydrochloric acid
  2. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give (R)-3-phenyl

Sources & evidence

ORD record
ord-f9f9ae3d854d48cc89f2314aaaa96443
Source dataset
uspto-grants-1994_05
Patent number
US05314896

Reaction notes

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