Hydrochloric Acid → HCID 21962625, compound

HRID 1070881Notes

Reaction equation

HRID 1070881 reaction equation
[CH3:1][C:2]1[C:3]([CH2:16][C:17]2[O:21][C:20]([C:22]([O:24]C)=[O:23])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[C:3]([CH2:16][C:17]2[O:21][C:20]([C:22]([OH:24])=[O:23])=[CH:19][CH:18]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21962618HCID 21962618, compound

Product 1

HCID 21962625HCID 21962625, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution containing Methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl) methyl]-2-furoate, 6, (15.1 g, 44 mmol) in MeOH (175 mL) and water (175 mL), a solution of NaOH (3.53 g, 88.3 mmol) in water (29 mL) was added. The reaction was stirred overnight at room temperature. After completion as judged by TLC, the solution was acidified with 1 M HCl to pH 2. The crude product was extracted in to organic layer using ethyl acetate and concentrated to afford 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid, 7 (15.0 g, 99% yield).

Workup

  1. extractionThe crude product was extracted in to organic layer
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9fa17b5e675144c4a44ba9ed03483700
Source dataset
uspto-grants-2005_06
Patent number
US06903132B2

Reaction notes

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