Hydrochloric Acid → 2-(1-Ethenyl-3,3,5,5-tetramethylcyclohexyl)acetic acid

HRID 2307082Notes

Reaction equation

HRID 2307082 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:20])[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]([CH2:14][C:15]([O:17]CC)=[O:16])([CH:12]=[CH2:13])[CH2:5]1.O.Cl>CO>[CH3:3][C:4]1([CH3:20])[CH2:9][C:8]([CH3:10])([CH3:11])[CH2:7][C:6]([CH2:14][C:15]([OH:17])=[O:16])([CH:12]=[CH2:13])[CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22630160HCID 22630160, compound

Product 1

HCID 226301322-(1-Ethenyl-3,3,5,5-tetramethylcyclohexyl)acetic acidYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of NaOH (1.03 g, 25.8 mmol) and acetate 16 (1.3 g, 5.15 mmol) in methanol (26 ml) was refluxed for 3 h. The mixture was cooled to room temperature and poured into water (100 ml). The aqueous phase was acidified by conc. aqueous HCl and extracted with hexane (330 ml). The combined organic phases were washed with brine and dried over CaCl2, filtered and evaporated. The residue was purified by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1) to give 17 (0.7 g, 71%) as a colorless solid with m.p. 92-94° C. 1H-NMR (CDCl3, TMS): 0.92 (6H, s, 3,5-CH3); 1.02 (6H, s, 3,5-CH3); 1.00-1.30 (4H, m, 4-CH2 and 2,6-CH); 1.90 (2H, d, 14 Hz, 2,6-CH); 2.27 (2H, s, CH2C═O); 5.11 and 5.13 (total 2H, both d, 11 and 18 Hz, ═CH2); 5.99 (1H, dd, 18 and 11 Hz, ═CH) and 10.80 ppm (1H, br s, COOH).

Workup

  1. extractionextracted with hexane (330 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over CaCl2
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-0d74e1cfeae242f889e4b751d38b1af2
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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