(Z)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoic acid → DA-E 5090

HRID 654709Notes

Reaction equation

HRID 654709 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:21]COC)=[C:6]([O:19][CH3:20])[CH:7]=[C:8]2/[CH:13]=[C:14](/[CH3:18])\[C:15]([OH:17])=[O:16])[CH3:2]>CC(C)=O>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:21])=[C:6]([O:19][CH3:20])[CH:7]=[C:8]2/[CH:13]=[C:14](/[CH3:18])\[C:15]([OH:17])=[O:16])[CH3:2]

Participants

3

Reactant 1

HCID 11724177(Z)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoic acid

Product 1

HCID 6438615DA-E 5090Yield 87.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

66 g of (Z)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoic acid was dissolved in 700 ml of acetone in which nitrogen had been preliminarily bubbled, and 43 ml of concentrated hydrochloric acid was gradually added while stirring at room temperature in a stream of nitrogen under light-shielded conditions. After stirring at room temperature for 1.5 hours, the reaction mixture was gradually poured into water to crystalize. The crystals were filtered, washed with water and dried to obtain 50.0 g of the titled compound as yellow crystals.

Workup

  1. customhad been preliminarily bubbled
  2. addition43 ml of concentrated hydrochloric acid was gradually added
  3. stirringAfter stirring at room temperature for 1.5 hours
  4. additionthe reaction mixture was gradually poured into water
  5. customto crystalize
  6. filtrationThe crystals were filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6c465b43efdd480a8980b79b42bc28bb
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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