Methanol → HCID 57136608, compound

HRID 1857887Notes

Reaction equation

HRID 1857887 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. customthe organic phase is separated 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-536f7a2619ce427492b83514ba2cf754
Source dataset
uspto-grants-2000_11
Patent number
US06147255

Reaction notes

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