Methanol → HCID 57136608, compound

HRID 2417331Notes

Reaction equation

HRID 2417331 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([CH3:21])=[CH:19][C:18]3[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:26](=[CH2:30])[C:27]([OH:29])=[O:28].CO.[CH2:33]1COCC1.S(=O)(=O)(O)O>O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([CH3:21])=[CH:19][C:18]3[C:17]([CH3:23])([CH3:22])[CH2:16][CH2:15][C:14]([CH3:25])([CH3:24])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:26](=[CH2:30])[C:27]([O:29][CH3:33])=[O:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 57093068HCID 57093068, compound

Product 1

HCID 57136608HCID 57136608, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.9 g (4.35 mmol) of 2-methoxymethoxy-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenylacrylic acid, 20 ml of methanol and 30 ml of THF are introduced into a round-bottomed flask. 2.8 ml of concentrated sulphuric acid are added and the mixture is stirred at room temperature for 12 hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is. separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. 1.63 g (95%) of methyl 2-hydroxy-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenylacrylate are collected.

Workup

  1. extractionextracted with ethyl ether
  2. customseparated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom1.63 g (95%) of methyl 2-hydroxy-5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenylacrylate are collected

Sources & evidence

ORD record
ord-69bbacce45f44f258f788f11b1a3c87a
Source dataset
uspto-grants-2004_11
Patent number
US06825360B1

Reaction notes

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