Hydrochloric Acid → 4-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

HRID 260587Notes

Reaction equation

HRID 260587 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]#N)=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-:25].[Na+].[OH2:27].Cl>C(O)C>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:27])=[O:25])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 148505774-Cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

Product 1

HCID 148505784-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g (0.063 mol) of 4-cyanobenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl ether were refluxed with 163 ml of 10N sodium hydroxide solution in 245 ml of ethanol for 2 h. The mixture was cooled and then poured into water, which was then acidified with hydrochloric acid, and the precipitate was filtered off with suction and washed with water and methanol. Drying resulted in 19.7 g of the title compound of melting point >330° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with water and methanol
  4. customDrying

Sources & evidence

ORD record
ord-d813fabc7ce74174a516d8d92719ac89
Source dataset
uspto-grants-1996_06
Patent number
US05527945

Reaction notes

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